(4-Amino-3-iodophenyl)acetic acid → Methyl (4-amino-3-iodophenyl)acetate

HRID 2173405Notes

Reaction equation

HRID 2173405 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[I:12].[CH3:13]O.Cl>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:13])=[O:10])=[CH:4][C:3]=1[I:12]

Participants

4

Reactant 2

HCID 14777512(4-Amino-3-iodophenyl)acetic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 46941390Methyl (4-amino-3-iodophenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude (4-amino-3-iodophenyl)acetic acid (about 40 g, about 171 mmol) in methanol (110 mL) was added 100 mL of 4 M MeOH/HCl and the solution was stirred at ambient temperature over night. Distilled the solution under reduce pressure, and the residue was purified by silica gel cloumn chromatography to give methyl (4-amino-3-iodophenyl)acetate. 1H-NMR (300 MHz, CDCl3) δ ppm 7.54 (s, 1H), 7.04 (d, J=7.9 Hz, 1H), 6.68 (d, J=7.9 Hz, 1H), 3.67 (s, 3H), 3.46 (s, 2H).

Workup

  1. distillationDistilled the solution
  2. customthe residue was purified by silica gel cloumn chromatography

Sources & evidence

ORD record
ord-7ea11bfdf602426b9e245f3f5020df4c
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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