Hydrochloric Acid → 6-Hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 653123ノート

反応式

HRID 653123 の反応式
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][CH2:7][C:6]2=[O:17].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][CH2:7][C:6]2=[O:17]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 145014416-Methoxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 212948076-Hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline収率 82.6%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of 6-methoxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.957 g) and aluminum chloride (3.359 g) in benzene (42 ml) was heated at 60° to 65° with stirring for 4 hours. To the aluminum chloride complex was added a mixture of crushed ice and 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (30 g) with a mixture of chloroform and methanol (50:1 to 10:1) as an eluent. The eluates were evaporated in vacuo to give 6-hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.52 g).

後処理

  1. temperaturewas heated at 60° to 65°
  2. additionTo the aluminum chloride complex was added
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (30 g) with a mixture of chloroform and methanol (50:1 to 10:1) as an eluent
  8. customThe eluates were evaporated in vacuo

出典と根拠

ORDレコード
ord-55e9eda95ba84f9ab1a377be05d8c73c
出典データセット
uspto-grants-1987_06
特許番号
US04675324

反応ノート

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