Ammonia → 4-Aminomethyl-3-nitrobenzoic acid

4-(Bromomethyl)-3-nitrobenzoic acid (3.2 g; 12.3 mmol) was dissolved in 8% NH3 in EtOH (300 mL) and the resulting solution was stirred at room temperature. After 22 h the solution was evaporated and the residue suspended in H2O (70 mL). The suspension was stirred for 15 min and filtered. The collected solid was suspended in H2O (40 mL) and dissolved by the addition of few drops of 25% aq. NH4OH (pH. 12), then the pH of the solution was adjusted to 6 by addition of 6 N HCl. The precipitated solid was filtered, and washed sequentially with MeOH (3×5 mL), and Et2O (10 mL) and was vacuum dried (1.3 kPa; P2O5) to give 4-(aminomethyl)-3-nitrobenzoic acid as a pale brown solid (1.65 g; 8.4 mmol). Yield 68%.

1. customAfter 22 h the solution was evaporated
2. stirringThe suspension was stirred for 15 min
3. filtrationfiltered
4. dissolutiondissolved by the addition of few drops of 25% aq. NH4OH (pH. 12)
5. additionthe pH of the solution was adjusted to 6 by addition of 6 N HCl
6. filtrationThe precipitated solid was filtered
7. washwashed sequentially with MeOH (3×5 mL), and Et2O (10 mL)
8. dry with materialdried (1.3 kPa; P2O5)

ORD record

ord-7d374b85cf2b45579f89e84847db1362

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07611692B2