Hydrochloric Acid → 2-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carboxylic acid

HRID 416580Notes

Reaction equation

HRID 416580 reaction equation
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]#N)=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4].[OH-:18].[K+].Cl.[OH2:21]>C(O)C>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]([OH:21])=[O:18])=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 222664592-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

Product 1

HCID 222665212-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-012) (260 mg, 1.13 mmol) was dissolved in water (6 mL)/ethanol (26 mL), to the reaction mixture was added potassium hydroxide (444 mg, 7.91 mmol), and the reaction mixture was heated under reflux for 24 h, and then cooled under ice-cooling. To the reaction mixture was added dropwise diluted hydrochloric acid (2 mol/L, 8 mL) and the reaction mixture was extracted with ethyl acetate (70 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The crystal residue was recrystallized from hexane to give 2-butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carboxylic acid (4-501-05) (197 mg, 70%) as a white crystal.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 24 h
  3. temperaturecooled under ice-
  4. temperaturecooling
  5. extractionthe reaction mixture was extracted with ethyl acetate (70 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe crystal residue was recrystallized from hexane

Sources & evidence

ORD record
ord-e565fed6eb124fe39d65411d73b33897
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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