(3-Amino-4-hydroxyphenyl)acetic acid → 5-Benzoxazoleacetic acid, 2-(4-chlorophenyl)-

HRID 1658151Notes

Reaction equation

HRID 1658151 reaction equation
CCO[CH2:4][CH3:5].[ClH:6].[NH2:7][C:8]1[CH:9]=[C:10]([CH2:15][C:16]([OH:18])=[O:17])[CH:11]=[CH:12][C:13]=1[OH:14]>CO>[Cl:6][C:8]1[CH:9]=[CH:10][C:4]([C:5]2[O:14][C:13]3[CH:12]=[CH:11][C:10]([CH2:15][C:16]([OH:18])=[O:17])=[CH:9][C:8]=3[N:7]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 1473103(3-Amino-4-hydroxyphenyl)acetic acidHCID 10953452Ether hydrochloride

Product 1

HCID 30397785-Benzoxazoleacetic acid, 2-(4-chlorophenyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of p-chlorobenzimidoethyl ether hydrochloride (16.5 g.) and 3-amino-4-hydroxyphenylacetic acid (12.53 g.) in methanol (75 ml.) was refluxed for 2 hours. After standing at room temperature overnight the white solid product was removed by filtration. Re-crystallisation from ethanol gave the required acid, m.p. 241°-242°C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customthe white solid product was removed by filtration

Sources & evidence

ORD record
ord-48d6624345e648808b536f9b4beaf16d
Source dataset
uspto-grants-1976_06
Patent number
US03962452

Reaction notes

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