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

HRID 35673Notes

Reaction equation

HRID 35673 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3e8091f2041c485398e065949e5b3af1
Source dataset
uspto-grants-1988_08
Patent number
US04767780

Reaction notes

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