4-Aminophenylacetic acid → HCID 67021355, compound

HRID 1660935Notes

Reaction equation

HRID 1660935 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1.CO.O1CCOC[CH2:25]1>>[CH3:25][O:20][C:19](=[O:21])[CH2:18][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 145334-Aminophenylacetic acidHCID 27357814-Chloro-3-nitropyridineHCID 21966525Dioxane Methanol

Product 1

HCID 67021355HCID 67021355, compound

Procedure

A mixture of 4-chloro-3-nitropyridine (0.500 g, 3.06 mmol) (LANCASTER) and (4-aminophenyl)-acetic acid (0.467 g 3.06 mmol) (Aldrich) in MeOH/dioxane (10 mL, 1/1 v/v) is stirred and refluxed for 6 h. The mixture is allowed to cool to rt and concentrated in vacuo to afford crude [4-(3-nitro-pyridin-4-ylamino)-phenyl]-acetic acid methyl ester. A suspension of the crude ester (0.569 g) and Raney Ni (˜0.140 g) in MeOH (15 mL) is stirred for 21 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of Celite and concentrated. Trituration of the residue in CH2Cl2 affords the title compound as a beige solid: ES-MS: 258.0 [M+H]+; single peak at tR=2.54 min (System 1).

Workup

  1. temperaturerefluxed for 6 h
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46189c3fc17549b386d51a9aa8dd58d4
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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