3-Aminophenol → HCID 86592253, compound

HRID 456677Notes

Reaction equation

HRID 456677 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:3]=1[C:4]([C:6]1[NH:10][C:9]([C:11]([OH:13])=O)=[CH:8][CH:7]=1)=[O:5].ClC1C=CC([N+]([O-])=O)=CC=1C(C1NC(C(Cl)=O)=CC=1)=O.C(Cl)(=O)C(Cl)=O.[NH2:47][C:48]1[CH:49]=[C:50]([OH:54])[CH:51]=[CH:52][CH:53]=1>>[OH:54][C:50]1[CH:49]=[C:48]([NH:47][C:11]([C:9]2[NH:10][C:6]([C:4](=[O:5])[C:3]3[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:2]=3[Cl:1])=[CH:7][CH:8]=2)=[O:13])[CH:53]=[CH:52][CH:51]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 65578Oxalyl chlorideHCID 18436887HCID 18436887, compoundHCID 18436888HCID 18436888, compound

Product 1

HCID 86592253HCID 86592253, compoundYield 51.6%

Procedure

5-(2-Chloro-5-nitro-benzoyl)-1H-pyrrole-2-carboxylic acid (200 mg) (Example 63) was converted to 5-(2-chloro-5-nitro-benzoyl)-1H-pyrrole-2-carbonyl chloride using oxalyl chloride at room temperature for one hour. It was then condensed with 3-amino-phenol (170 mg, 1.7 eq.) and TEA at room temperature for 1.5 hrs to give 135 mg of 5-(2-chloro-5-nitro-benzoyl)-1H-pyrrole-2-carboxylic acid (3-hydroxy-phenyl)-amide.

Workup

  1. customat room temperature
  2. customfor one hour

Sources & evidence

ORD record
ord-0c38ce56c7084cafad47b28f06e3a7a8
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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