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

HRID 35673ノート

反応式

HRID 35673 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 The extract
  4. washwas 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-3e8091f2041c485398e065949e5b3af1
出典データセット
uspto-grants-1988_08
特許番号
US04767780

反応ノート

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