Methanol → Methyl 2-(3-aminophenyl)acetate hydrochloride

HRID 1197698Notes

Reaction equation

HRID 1197698 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[CH3:16][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 44119610Methyl 2-(3-aminophenyl)acetate hydrochlorideYield 96.8%

Procedure

A suspension of 3-amino phenylacetic acid (5.0 g, 33 mmol) in methanol (50 ml) at 0° C. under argon was slowly treated with thionyl chloride (19.4 g, 165 mmol). After completion of addition, the reaction mixture was allowed to warm up to room temperature and stirred for 16 hours. The solvent was evaporated and the residue was triturated with ethyl ether to give 3-amino phenylacetic acid methylester hydrochloride (5.3 g, 96.8%) as a colorless solid. 1H NMR (CDCl3) δ 10.6 (s, 2 H), 7.42 (m, 4 H), 3.68 (s, 3 H). 3.66 (s,2 H); 13C NMR (CDCl3) 172.5, 137.3, 133.1, 131.2, 130.8, 125.9, 123.7, 53.5, 41.5.

Workup

  1. additionAfter completion of addition
  2. customThe solvent was evaporated
  3. customthe residue was triturated with ethyl ether

Sources & evidence

ORD record
ord-456356244095428cb1df3f299d94bbd8
Source dataset
uspto-grants-1994_01
Patent number
US05276168

Reaction notes

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