2-Chlorobenzaldehyde → {[4-(2-Chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetic acid

HRID 2290324ノート

反応式

HRID 2290324 の反応式
C[O:2][C:3]([CH2:5][O:6][CH2:7][C:8](=O)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:4].[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O.[NH2:25]/[C:26](/[CH3:32])=[CH:27]\[C:28]([O:30][CH3:31])=[O:29]>CO>[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]1[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([CH3:32])[NH:25][C:8]([CH2:7][O:6][CH2:5][C:3]([OH:2])=[O:4])=[C:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

参加物

5

反応物 3

HCID 69962-ChlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 13457217Ethyl 4-(methoxycarbonylmethoxy)acetoacetate

生成物 1

HCID 13457220{[4-(2-Chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetic acid収率 16.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of ethyl 4-(methoxycarbonylmethoxy)acetoacetate (200 g), 2-chlorobenzaldehyde (128.8 g) and methyl 3-aminocrotonate (105.4 g) in methanol (600 ml) was heated under reflux for 16 hours and then evaporated. The residue was treated with 10% aqueous sodium hydroxide solution and the mixture heated under reflux for 1.5 hours, allowed to cool to room temperature, washed three times with dichloromethane, acidified with concentrated hydrochloric acid and extracted into dichloromethane. The dichloromethane extracts were washed with water, dried over magnesium sulphate and evaporated. The residue was recrystallised from ethyl acetate to give the title compound (63 g), m.p. 150°-154° C.

後処理

  1. temperatureunder reflux for 16 hours
  2. customevaporated
  3. additionThe residue was treated with 10% aqueous sodium hydroxide solution
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 1.5 hours
  6. washwashed three times with dichloromethane
  7. extractionextracted into dichloromethane
  8. washThe dichloromethane extracts were washed with water
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. customThe residue was recrystallised from ethyl acetate

出典と根拠

ORDレコード
ord-388d6421a02a48e1832a690c48bc6945
出典データセット
uspto-grants-1986_10
特許番号
US04616024

反応ノート

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