Methanol → Methyl 2-(4-aminophenyl)acetate

HRID 1855211Notes

Reaction equation

HRID 1855211 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:16]O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:16])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 145334-Aminophenylacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 2761030Methyl 2-(4-aminophenyl)acetateYield 99%

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(4-aminophenyl)acetic acid (B−1) (10 g, 66.16 mmol) in methanol (50 mL) was added dropwise SOCl2 (5 mL). The mixture was stirred at 60° C. for 6 h. After evaporated the solvent, the residue was recrystallized with Et2O to afford the product (10.9 g, 99%) as a yellow solid. LC-MS: (M+H)+=166;

Workup

  1. customAfter evaporated the solvent
  2. customthe residue was recrystallized with Et2O

Sources & evidence

ORD record
ord-5c0999d516c4481f9fee5c817bff1a69
Source dataset
uspto-grants-2015_02
Patent number
US08962855B2

Reaction notes

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