2-Amino-4-chlorophenol → HCID 17296978, compound

HRID 842116Notes

Reaction equation

HRID 842116 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([OH:23])=O.[OH:24][C:25]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:26]=1[NH2:27]>ClCCl.O>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([NH:27][C:26]1[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:25]=1[OH:24])=[O:23]

Participants

6

Reactant 3

HCID 72652-Amino-4-chlorophenolHCID 17124o-Chlorophenylacetic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 17296978HCID 17296978, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1,1′-carbonyl diimidazole (66.5 g, 0.41 mol) and dichloromethane (300 ml) was added 2-chlorophenylacetic acid (67.0 g, 0.39 mol) dissolved in dichloromethane (200 ml). The mixture was stirred for 1.5 hours and 2-hydroxy-5-chloroaniline (56.4 g, 0.39 mol) was added in one portion. After stirring overnight, the reaction mixture was diluted with water and the mixture was filtered to give the desired amide. The dichloromethane was separated and washed with water. Evaporation of the dichloromethane under reduced pressure afforded additional product which was triturated with a small amount of dichloromethane and combined with the material collected previously to give 108.5 g of the title compound.

Workup

  1. stirringAfter stirring overnight
  2. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-4b712830c9cb4a319cab8f3b9398aaa1
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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