Water → HCID 13219213, compound

HRID 615180Notes

Reaction equation

HRID 615180 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH2:12][OH:13])=[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][CH:26]([CH3:28])[CH3:27])=[O:24])=[C:4]([CH3:29])[N:3]=1.[C:30](Cl)(=[O:32])[CH3:31].O>N1C=CC=CC=1>[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH2:12][O:13][C:30](=[O:32])[CH3:31])=[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][CH:26]([CH3:27])[CH3:28])=[O:24])=[C:4]([CH3:29])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 10431202Nimodipine Metabolite 3

Product 1

HCID 13219213HCID 13219213, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20.1 g (50 mmols) of 2-hydroxyethyl isopropyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (Example 1) were dissolved in 75 ml of pyridine. 5.9 g (75 mmoles) of acetyl chloride were added to this. After the exothermic reaction was over, the reaction mixture was stirred at room temperature for 3 hours, poured into water and extracted with CH2Cl2. The organic extracts were washed with dilute hydrochloric acid and, after drying over sodium sulphate, evaporated in vacuo. The resulting oil crystallized completely, it was stirred with petroleum ether, filtered off with suction and dried.

Workup

  1. customAfter the exothermic reaction
  2. extractionextracted with CH2Cl2
  3. washThe organic extracts were washed with dilute hydrochloric acid
  4. dry with materialafter drying over sodium sulphate
  5. customevaporated in vacuo
  6. customThe resulting oil crystallized completely
  7. stirringit was stirred with petroleum ether
  8. filtrationfiltered off with suction
  9. customdried

Sources & evidence

ORD record
ord-c03ba24391774182947a636a922f9cc1
Source dataset
uspto-grants-1985_02
Patent number
US04497821

Reaction notes

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