2,3,5,6,7,8-Hexahydro-1-methyl-3-oxo-7-(4-pyridinyl)-4-isoquinolinecarbonitrile → 5,6,7,8-Tetrahydro-1-methyl-7-(4-pyridinyl)-3(2h)-isoquinolinone

HRID 980910Notes

Reaction equation

HRID 980910 reaction equation
C([C:3]1[C:4](=[O:20])[NH:5][C:6]([CH3:19])=[C:7]2[C:12]=1[CH2:11][CH2:10][CH:9]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH2:8]2)#N>S(=O)(=O)(O)O>[CH3:19][C:6]1[NH:5][C:4](=[O:20])[CH:3]=[C:12]2[C:7]=1[CH2:8][CH:9]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH2:10][CH2:11]2

Participants

3

Reactant 1

HCID 136327302,3,5,6,7,8-Hexahydro-1-methyl-3-oxo-7-(4-pyridinyl)-4-isoquinolinecarbonitrile

Product 1

HCID 137720565,6,7,8-Tetrahydro-1-methyl-7-(4-pyridinyl)-3(2h)-isoquinolinoneYield 83.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Cyano-2,3,5,6,7,8-hexahydro-1-methyl-3-oxo-7-(4-pyridyl)isoquinoline (0.5 g) was dissolved in 85% sulfuric acid, and the solution was heated under reflux at 180°-200° C. for 5 hours. After cooling the reaction mixture was poured into ice water. Deposited crystals were filtered out and then purified to obtain 0.38 g of 2,3,5,6,7,8-hexahydro-1-methyl-3-oxo-7-(4-pyridyl)isoquinoline.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux at 180°-200° C. for 5 hours
  3. temperatureAfter cooling the reaction mixture
  4. filtrationDeposited crystals were filtered out
  5. custompurified

Sources & evidence

ORD record
ord-3070b1456c0a47858e683a79e8569ccc
Source dataset
uspto-grants-1987_01
Patent number
US04639521

Reaction notes

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