Dimethyl acetylenedicarboxylate → HCID 178498488, compound

HRID 1287501Notes

Reaction equation

HRID 1287501 reaction equation
CO[C:3]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[C:13]=1[CH3:19]>CO>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:3]([OH:4])[C:17]2[C:12](=[C:13]([CH3:19])[C:14]3[N:18]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:3]([OH:4])[C:15]=3[CH:16]=2)[N:11]=1)=[O:8]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 132052,6-Toluenediamine

Product 1

HCID 178498488HCID 178498488, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of acetylene dicarboxylic acid dimethyl ester (2.8g.) in dry methanol (20ml.) was added to a solution of 2,6-diamino-1-methylbenzene (1.2g.) in dry methanol (20ml.), and the mixture heated under reflux for 3 hours. The mixture was then cooled and filtered, and the solid residue of bis anil (1.9g., m.p. 194°-196°C., crystallised from dimethylformamide) was added in portions to boiling diphenyl ether (50ml.), and the mixture was kept at 240°-145°C. for 10 minutes. The mixture was then cooled, and filtered, and the solid residue was washed with petroleum ether (b.p. 40°-60°C.; 750ml.), and crystallised from dimethylsulphoxide to give 2,8-dimethoxycarbonyl-4,6-dihydroxy-10-methylpyrido[3,2-g]quinoline, m.p. 296°C.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered
  5. customthe solid residue of bis anil (1.9g., m.p. 194°-196°C., crystallised from dimethylformamide)
  6. additionwas added in portions
  7. temperatureThe mixture was then cooled
  8. filtrationfiltered
  9. washthe solid residue was washed with petroleum ether (b.p. 40°-60°C.; 750ml.)
  10. customcrystallised from dimethylsulphoxide

Sources & evidence

ORD record
ord-cce482be225e45189d85259e0b9cf697
Source dataset
uspto-grants-1976_10
Patent number
US03984551

Reaction notes

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