4-Aminophenylacetic acid → (4-Hydrazinophenyl)acetic acid hydrochloride

Temperature

2 °C

To a solution containing conc. HCl (76 ml) and 4-amino phenylacetic acid (10 g: 66 mmol) at 40° C. was added a solution of sodium nitrite (4.56 g; 55 mmol) in water (10 ml) dropwise, while maintaining the temperature at 0 to 4° C. The mixture was stirred for 30 minutes and added to a cold (0° C.) solution of SnCl2 (74.5 g 331 mmol) in conc. HCl (50 ml). The mixture was left to warm to room temperature overnight. The precipitate formed was filtered and washed with water (50 ml), 50% aq.HCl (50 ml), water (50 ml) and ether (2×50 ml). The solid was dried in vacuo to give the product 13 g. M.pt. 220-223° C. dec.

1. waitThe mixture was left
2. temperatureto warm to room temperature overnight
3. customThe precipitate formed
4. filtrationwas filtered
5. washwashed with water (50 ml), 50% aq
6. customThe solid was dried in vacuo

ORD record

ord-196937e2ce99451e8fe4874d78b7c69e

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06103752