Sodium Methoxide → 11-Chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione

HRID 579875Notes

Reaction equation

HRID 579875 reaction equation
C([N:4]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[C:9]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:8]=2[CH2:7][CH2:6][C:5]1=[O:20])(=O)C.C[O-].[Na+]>CO>[Cl:19][C:17]1[CH:16]=[CH:15][C:9]2[C:10](=[O:14])[CH2:11][CH2:12][CH2:13][NH:4][C:5](=[O:20])[CH2:6][CH2:7][C:8]=2[CH:18]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 198331174-Acetyl-11-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione

Product 1

HCID 1983315911-Chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.05 g (7 mmol) of 4-acetyl-11-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione in 30 ml of methanol was treated with 0.85 g (15.4 mmol) of sodium methanolate, stirred at room temperature for 2 hours, the reaction mixture was concentrated in vacuo, treated with water and extracted at pH 14 with chloroform. After drying the chloroform phase with sodium sulphate and distillation of the solvent in vacuo there was obtained 11-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione of melting point 142°-144°.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiontreated with water
  3. extractionextracted at pH 14 with chloroform
  4. dry with materialAfter drying the chloroform phase
  5. distillationwith sodium sulphate and distillation of the solvent in vacuo

Sources & evidence

ORD record
ord-1272cb94af2545cf90e6d093062ea7a0
Source dataset
uspto-grants-1988_06
Patent number
US04749791

Reaction notes

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