Acetic Anhydride → 2-(4-acetamidophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one

HRID 2231214Notes

Reaction equation

HRID 2231214 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[CH2:16][CH:15]3[C:10]([C:11]4[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:12]=4[CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[C:24]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[CH2:16][CH:15]3[C:10]([C:11]4[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:12]=4[CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1)(=[O:26])[CH3:25]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 212863822-(4-aminophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one

Product 1

HCID 212863852-(4-acetamidophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one

Procedure

A mixture of 2-(4-aminophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one in acetic anhydride is refluxed under heating for 8 hours. After the acetic anhydride is distilled off, the residue is extracted with chloroform. The extract is washed with water and dried over magnesium sulfate anhydride. The chloroform is distilled off to give 2-(4-acetamidophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 8 hours
  3. distillationAfter the acetic anhydride is distilled off
  4. extractionthe residue is extracted with chloroform
  5. washThe extract is washed with water
  6. dry with materialdried over magnesium sulfate anhydride
  7. distillationThe chloroform is distilled off

Sources & evidence

ORD record
ord-9642f7722cbb4670b3c1b20e32a69b0a
Source dataset
uspto-grants-1988_11
Patent number
US04782057

Reaction notes

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