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

HRID 35673노트

반응식

HRID 35673 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3e8091f2041c485398e065949e5b3af1
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767780

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