Hydrochloric Acid → HCID 68704387, compound

HRID 655214Notes

Reaction equation

HRID 655214 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]C(=O)C)=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1.[ClH:19]>>[ClH:19].[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:18])=[O:2])=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 21941232HCID 21941232, compound

Product 1

HCID 68704387HCID 68704387, compound

Procedure

A solution of (4-acetylamino-3-nitro-phenyl)-acetic acid methyl ester (1.3 g, 5.15 mmol) in 6 N aqueous hydrochloric acid (10 mL) was stirred at reflux for 1.5 h, then concentrated in vacuo to dryness. The residue was triturated with diethyl ether, filtered, washed with diethyl ether, and dried in vacuo to give 978 mg of product as a dark orange-yellow solid. 1H NMR 500 MHz (DMSO) δ 3.49 (s, 2H), 6.98 (d, 1H), 7.30 (dd, 1H), 7.86 (d, 1H); MS (m/z) 197 [M+H+]+.

Workup

  1. temperatureat reflux for 1.5 h
  2. concentrationconcentrated in vacuo to dryness
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. washwashed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4017815f43b14b41b823531133aea6f6
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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