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

HRID 745300Notes

Reaction equation

HRID 745300 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-af351d060f564348b9ccb3500af71c87
Source dataset
uspto-grants-1986_07
Patent number
US04598148

Reaction notes

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