4-Chlorophenol → HCID 10563608, compound

HRID 616102Notes

Reaction equation

HRID 616102 reaction equation
[H-].[Na+].CN(C)C=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[NH2:16][C:17]1[CH:22]=[C:21](Cl)[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]>O>[NH2:16][C:17]1[CH:22]=[C:21]([O:15][C:12]2[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=2)[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 10563608HCID 10563608, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.26 G. 57% sodium hydride in oil suspension in 20 ml. dimethylformamide is treated with 3.9 g. p-chlorophenol. When the mixture becomes homogenous, 2.5 g. 2-amino-4-chloro-1-nitrobenzene is added and the mixture heated for five hours at 130°-135° C. The crude product is obtained by diluting the reaction mixture with water and filtering and washing with water and hexane. Recrystallization from methanol gives pure 2-amino-4-(4-chlorophenoxy)-1-nitrobenzene.

Workup

  1. temperaturethe mixture heated for five hours at 130°-135° C
  2. customThe crude product is obtained
  3. filtrationfiltering
  4. washwashing with water and hexane
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-f80cd36266b34c64b3acc65b7c98b595
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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