Dimethylformamide → 4-Cyano-3-methoxy-1-methyl-5,6,7,8-tetrahydroisoquinoline

HRID 235588Notes

Reaction equation

HRID 235588 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH3:14])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[C:12]#[N:13].C[O-].[Na+].CN(C)[CH:20]=[O:21]>CO>[C:12]([C:11]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]([CH3:14])=[N:3][C:2]=1[O:21][CH3:20])#[N:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 37301863-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 132957574-Cyano-3-methoxy-1-methyl-5,6,7,8-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Chloro-4-cyano-1-methyl-5,6,7,8-tetrahydroisoquinoline (10.0 g) was refluxed with sodium methoxide (1.1 equiv) in a mixture of methanol (150 ml) and anhydrous dimethylformamide (20 ml) for 24 hr. The bulk of the solvent was evaporated under reduced pressure, water was added to the residue and the resulting mixture was extracted with ether. The dried (MgSO4) organic fraction was evaporated and the residue was purified by column chromatography over silica gel with dichloromethane elution to give 4-cyano-3-methoxy-1-methyl-5,6,7,8-tetrahydroisoquinoline as white crystals, mp 116° C. Pmr spectrum (CDCl3 ; δ in ppm): 1.81 (4H,m); 2.39 (3H,s); 2.50-2.94 (4H,m); 3.98 (3H, s).

Workup

  1. customThe bulk of the solvent was evaporated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe resulting mixture was extracted with ether
  4. dry with materialThe dried (MgSO4) organic fraction
  5. customwas evaporated
  6. customthe residue was purified by column chromatography over silica gel with dichloromethane elution

Sources & evidence

ORD record
ord-dc3f272c01c946c7b0f151d5dd8c51d6
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

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