Methods of producing compounds from 5-(halomethyl)furfural

1. A method of producing a compound of formula (J):

and/or a salt thereof, wherein R 1 and R 2 are each independently hydrogen or alkyl,

the method comprising:

combining a compound of formula (A) with ammonia in the presence of a copper catalyst to produce the compound of formula (J) and/or a salt thereof, wherein:

the compound of formula (A) is:

wherein:

R 1 and R 2 are as defined for formula (J) above, and

X is halo.

2. The method of claim 1 , wherein the salt of the compound of formula (J) is a compound of formula (J-X):

wherein:

R 1 and R 2 are as defined for formula (J) above, and

X is as defined for formula (A) above.

3. A method of producing a compound of formula (J-X):

wherein:

R 1 and R 2 are each independently hydrogen or alkyl, and

X is halo,

the method comprising:

combining a compound of formula (A) with liquid ammonia and acid to produce the compound of formula (J-X), wherein:

the acid is a Bronsted acid with a pKa equal to or lower than 9; and

the compound of formula (A) is:

wherein:

R 1 and R 2 are as defined for formula (J-X) above, and

X is halo.

4. The method of claim 3 , wherein the acid is HY, wherein Y is halo, and the method further comprises:

producing a compound of formula (J-Y) from at least a portion of the reaction mixture, wherein the compound of formula (J-Y) is:

wherein:

R 1 and R 2 are as defined for formula (J-X) above, and

Y is as defined for the acid.

5. A method of producing a compound of formula (J-X):

wherein:

R 1 and R 2 are each independently hydrogen or alkyl, and

X is halo,

the method comprising:

combining a compound of formula (A) with ammonia and a copper catalyst to produce a compound of formula (J) in a reaction mixture, wherein:

the compound of formula (A) is:

wherein:

R 1 and R 2 are as defined for formula (J-X) above, and

X is halo; and

the compound of formula (J) is:

wherein R 1 and R 2 are as defined for formula (J-X) above; and

adding an acid to the reaction mixture of step (b) to produce the compound of formula (J-X), wherein the acid is a Bronsted acid with a pKa equal to or lower than 9.

6. The method of claim 5 , wherein the acid is HY, wherein Y is halo, and wherein the adding of the acid to the reaction mixture of step (b) produces the compound of formula (J-X), or a compound of formula (J-Y), or a combination thereof, wherein the compound of formula (J-Y) is:

wherein:

R 1 and R 2 are as defined for formula (J-X) above, and

Y is as defined for the acid.

7. A method of producing a compound of formula (J-X):

wherein:

R 1 and R 2 are each independently hydrogen or alkyl, and

X is halo,

the method comprising:

a) combining a compound of formula (A) with ammonia and a copper catalyst to form a reaction mixture, wherein:

the compound of formula (A) is:

wherein:

R 1 and R 2 are as defined for formula (J-X) above, and

X is halo;

b) producing a compound of formula (J) from at least a portion of the reaction mixture, wherein the compound of formula (J) is:

wherein R 1 and R 2 are as defined for formula (J-X) above; and

c) isolating the compound of formula (J) produced; and

d) combining the isolated compound of formula (J) with an acid to produce the compound of formula (J-X), wherein the acid is a Bronsted acid with a pKa equal to or lower than 9.

8. The method of claim 7 , wherein the acid is HY, wherein Y is halo, and wherein the combining of the isolated compound of formula (J) with the acid produces the compound of formula (J-X), or a compound of formula (J-Y), or a combination thereof, wherein the compound of formula (J-Y) is:

wherein:

R 1 and R 2 are as defined for formula (J-X) above, and

Y is as defined for the acid.

9. A method of producing a compound of formula (I):

and/or a salt thereof, wherein R 1 and R 2 are each independently hydrogen or alkyl,

the method comprising:

producing a compound of formula (J) and/or a salt thereof according to the method of claim 1 , wherein:

the compound of formula (J) is:

and/or a salt thereof, wherein R 1 and R 2 are as defined for formula (I) above; and

reducing the compound of formula (J) and/or a salt thereof in the presence of additional ammonia to produce the compound of formula (H) and/or a salt thereof, wherein:

the compound of formula (H) is:

wherein R 1 and R 2 are as defined for formula (I) above; and

further reducing the compound of formula (H) and/or a salt thereof to produce the compound of formula (I) and/or a salt thereof.