Sodium Hydroxide → 1-Methyl-5,6,7,8-tetrahydroisoquinolin-3(2H)-one

HRID 980918Notes

Reaction equation

HRID 980918 reaction equation
C([C:3]1[C:4](=[O:14])[NH:5][C:6]([CH3:13])=[C:7]2[C:12]=1[CH2:11][CH2:10][CH2:9][CH2:8]2)#N.[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:13][C:6]1[NH:5][C:4](=[O:14])[CH:3]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13896753-Hydroxy-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile

Product 1

HCID 118193651-Methyl-5,6,7,8-tetrahydroisoquinolin-3(2H)-oneYield 78.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Cyano-2,3,5,6,7,8-hexahydro-1-methyl-3-oxoisoquinoline (1.88 g) was dissolved in 20 ml of 85% sulfuric acid, and the resultant solution was heated at 180°-190° C. for 10 hours. After cooling, the reaction mixture was poured into ice water and an aqueous sodium hydroxide solution was added to adjust the pH to about 5. Deposited crystals were filtered out and recrystallized from methanol. Thus, there was obtained 1.28 g of 2,3,5,6,7,8-hexahydro-1-methyl-3-oxoisoquinoline.

Workup

  1. temperatureAfter cooling
  2. filtrationDeposited crystals were filtered out
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b0394fa40f564caa96d953cc0119175c
Source dataset
uspto-grants-1987_01
Patent number
US04639521

Reaction notes

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