Nitric Acid → Nimodipine Metabolite 3

HRID 247049ノート

反応式

HRID 247049 の反応式
[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[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][CH2:11][CH2:12][OH:13])=[O:9].[N+]([O-])(O)=O.[OH-].[Na+]>O>[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]([CH3:27])[CH3:28])=[O:24])=[C:4]([CH3:29])[N:3]=1

参加物

5

反応物 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 104538601,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-isopropyl 5-(2-hydroxyethyl) ester

生成物 1

HCID 10431202Nimodipine Metabolite 3

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

20 g (49.5 mmol) of 2-hydroxyethyl isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate were introduced into a mixture of 83 ml of 96% strength nitric acid in 660 ml of water and heated to boiling for 1 hour. The mixture was then cooled down to 5° to 10° C. and made weakly alkaline with dilute sodium hydroxide solution. The oil which had separated out was extracted with methylene chloride, the extracts were dried over sodium sulphate and evaporated in vacuo. The oily residue was induced to crystallize by trituration with ether/petroleum ether, filtered off with suction and recrystallized from methanol.

後処理

  1. temperatureheated
  2. temperatureThe mixture was then cooled down to 5° to 10° C.
  3. customThe oil which had separated out
  4. extractionwas extracted with methylene chloride
  5. dry with materialthe extracts were dried over sodium sulphate
  6. customevaporated in vacuo
  7. customto crystallize by trituration with ether/petroleum ether
  8. filtrationfiltered off with suction
  9. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-007092b5341c459183e2d66331e5ea72
出典データセット
uspto-grants-1987_11
特許番号
US04705794

反応ノート

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