Sodium Hydroxide → 2-(6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidene)acetamide

HRID 1979716Notes

Reaction equation

HRID 1979716 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[CH:15][C:16]#[N:17])[NH:8][CH2:7][CH2:6]2.[OH-:18].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[CH:15][C:16](=[O:18])[NH2:17])[NH:8][CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 419389(6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidene)acetonitrile

Product 1

HCID 704697252-(6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidene)acetamide

Procedure

Polyphosphoric acid (10.0 g) is heated to 100° C. and 1.0 g of 6,7-dimethoxy-1-cyanomethylene-1,2,3,4-tetrahydroisoquinoline is added under mechanical stirring. The reaction mixture is heated for 1 hour, poured into crushed ice and made basic with 30% sodium hydroxide. The mixture is extracted with chloroform and the extract dried over anhydrous sodium sulfate. The solvent is evaporated under reduced pressure to give a white solid, yield 0.7 g, mp. 156°-158° C.

Workup

  1. temperatureThe reaction mixture is heated for 1 hour
  2. additionpoured
  3. custominto crushed ice
  4. extractionThe mixture is extracted with chloroform
  5. dry with materialthe extract dried over anhydrous sodium sulfate
  6. customThe solvent is evaporated under reduced pressure
  7. customto give a white solid, yield 0.7 g, mp. 156°-158° C.

Sources & evidence

ORD record
ord-cf7b7e0ab3834c05ae019129caa89e01
Source dataset
uspto-grants-1984_11
Patent number
US04482556

Reaction notes

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