Acetic Anhydride → HCID 13067126, compound

HRID 2296292Notes

Reaction equation

HRID 2296292 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH:14]=[C:13]2[C:7]([CH2:8][N+:9]([O-])=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:11]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:12]=32)=[CH:6]1)=[O:4].[C:28]([O:31]C(=O)C)(=[O:30])[CH3:29]>>[CH3:1][O:2][C:3]([N:5]1[CH:14]=[C:13]2[C:7]([CH:8]([O:31][C:28](=[O:30])[CH3:29])[N:9]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:11]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:12]=32)=[CH:6]1)=[O:4]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 13228385HCID 13228385, compound

Product 1

HCID 13067126HCID 13067126, compound

Procedure

A mixture of 7.6 g (19 mmol) of 8-chloro-6-(2-chlorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-carboxylic acid methyl ester 5-oxide and 200 ml of acetic anhydride was stirred at 70° for 12 hr and at 105° for 5 hr. The acetic anhydride solution was concentrated at reduced pressure. The residue was dissolved in methylene chloride and washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give an oil. Purification by column chromatography (50 g, neutral alumina; 5% ether in methylene chloride, eluent) gave a tan solid, mp 175°-177°. Recrystallization from ether gave an off-white solid, mp 177°-178°.

Workup

  1. concentrationThe acetic anhydride solution was concentrated at reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  4. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customto give an oil
  7. customPurification by column chromatography (50 g, neutral alumina; 5% ether in methylene chloride, eluent)
  8. customgave a tan solid, mp 175°-177°
  9. customRecrystallization from ether
  10. customgave an off-white solid, mp 177°-178°

Sources & evidence

ORD record
ord-072bd3a167564d159fb0a6d75781f2c7
Source dataset
uspto-grants-1984_01
Patent number
US04428878

Reaction notes

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