Nimodipine → Dehydro nimodipine

HRID 615181

Reaction equation

HRID 615181 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:30])=[C:5]([C:23]([O:25][CH2:26][CH2:27][O:28][CH3:29])=[O:24])[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:7]=1[C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9]>C(O)(=O)C.[O-2].[Cr+6].[O-2].[O-2]>[CH3:1][C:2]1[C:7]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:5]([C:23]([O:25][CH2:26][CH2:27][O:28][CH3:29])=[O:24])=[C:4]([CH3:30])[N:3]=1

Participants

4

Reactant 1

HCID 4497Nimodipine

Product 1

HCID 529928Dehydro nimodipine

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Procedure

6.8 g of chromium(VI) oxide were added in portions to a boiling solution of 41.8 g (100 mmols) of isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate in 160 ml of glacial acetic acid. The mixture was then heated under reflux for a further 30 minutes and, after cooling down, poured into ammoniacal ice-water. The mixture was extracted with chloroform and the extracts, after drying over sodium sulphate, were evaporated in vacuo. 35.9 g (86% of theory) of an oil resulted.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for a further 30 minutes
  3. temperatureafter cooling down
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialthe extracts, after drying over sodium sulphate
  6. customwere evaporated in vacuo
  7. custom35.9 g (86% of theory) of an oil resulted

Sources & evidence

ORD record
ord-0e7c6c54a4514adca34d6ba6b65b0a33
Source dataset
uspto-grants-1985_02
Patent number
US04497821

Linked notes

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