Dimethylformamide → 2'-Cyanomethylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline]

HRID 648103Notes

Reaction equation

HRID 648103 reaction equation
CN(C)C=O.[CH2:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2([CH2:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16]2)[CH2:8][NH:7]1.C(=O)(O)[O-].[Na+].Cl[CH2:30][C:31]#[N:32]>O>[C:31]([CH2:30][N:7]1[CH2:8][C:9]2([CH2:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16]2)[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6]1)#[N:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 516892Sodium BicarbonateHCID 15917444spiro[benzofuran-2(3H),4'(2'H)-isoquinoline]

Product 1

HCID 132645362'-Cyanomethylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline]

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To dry dimethylformamide is added spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (11.0 g), sodium bicarbonate (8.4 g) and chloroacetonitrile (6.8 g) and the mixture is heated to 70° for four hours. The dimethylformamide is evaporated to give an oil, which is stirred with water (300 ml) for 15 minutes and then extracted with ether/dichloromethane. The organic extract is washed with water (2X), saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After filtering, the solvents are evaporated to an oil which solidifies to the product (10.6 g), 83%), as an off-white solid upon trituration with petroleum ether/ether. For analysis, a sample is recrystallized twice from hexane/acetone to yield platelets.

Workup

  1. temperaturethe mixture is heated to 70° for four hours
  2. customThe dimethylformamide is evaporated
  3. customto give an oil, which
  4. extractionextracted with ether/dichloromethane
  5. extractionThe organic extract
  6. washis washed with water (2X), saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customthe solvents are evaporated to an oil which
  10. customFor analysis, a sample is recrystallized twice from hexane/acetone
  11. customto yield platelets

Sources & evidence

ORD record
ord-fc359672d031443485785603ea8bd0dd
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

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