Diethyl Carbonate → HCID 908572, compound

HRID 1979717Notes

Reaction equation

HRID 1979717 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](=[O:18])[NH2:17])[NH:8][CH2:7][CH2:6]2.[O-:19][CH2:20]C.[Na+].C(=O)(OCC)OCC>C(O)C>[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]1=[CH:15][C:16](=[O:18])[NH:17][C:20](=[O:19])[N:8]1[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 2723922Sodium ethoxideHCID 704697252-(6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidene)acetamide

Product 1

HCID 908572HCID 908572, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6,7-dimethoxy-1-carbamoylmethylene-1,2,3,4-tetrahydroisoquinoline (5.0g) and an excess of sodium ethoxide (prepared from 12.0 g of sodium metal and 600 ml of ethanol) in ethanol is heated. 150.0 ml of diethyl carbonate is added to the solution. The reaction mixture is refluxed for an additional 2.5 hr. The solvent is removed under vacuum and the residue is acidified to give a white precipitate, yield 4.80 g. The product crystallizes from dimethylformamide, mp. 323°-325° C.

Workup

  1. temperatureThe reaction mixture is refluxed for an additional 2.5 hr
  2. customThe solvent is removed under vacuum
  3. customto give a white precipitate, yield 4.80 g
  4. customThe product crystallizes from dimethylformamide, mp. 323°-325° C.

Sources & evidence

ORD record
ord-b7297953431d411e833d31b7237be5a5
Source dataset
uspto-grants-1984_11
Patent number
US04482556

Reaction notes

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