Ammonia → 7,8-Dimethoxypyrimido[4,5-b]Quinolin-4(3H)-One-2-Carboxamide

HRID 596596Notes

Reaction equation

HRID 596596 reaction equation
[NH3:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]1[N:16]=[C:17]([C:21]([O:23]CC)=O)[NH:18][C:19](=[O:20])[C:8]1=[CH:7]2>C(O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]1[N:16]=[C:17]([C:21]([NH2:1])=[O:23])[NH:18][C:19](=[O:20])[C:8]1=[CH:7]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 135445830Pirolate

Product 1

HCID 1357053247,8-Dimethoxypyrimido[4,5-b]Quinolin-4(3H)-One-2-Carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

Anhydrous ammonia is bubbled into a mixture of ethyl 7,8-dimethoxy-pyrimido[4,5-b]quinolin-4(3H)-one-2-carboxylate (300 mg., 9.00 millimoles) in absolute ethanol (75 ml.) for 15 minutes. A clear solution formed, followed, after a few minutes, by formation of a precipitate. The reaction mixture is transferred to a pressure bomb (Monel) and heated in a 95° C. oil bath overnight. The bomb is then cooled to room temperature and the contents removed. The bomb is washed with ethanol and the combined reaction mixture plus wash filtered to recover the product. The filter cake is washed with ethanol and then dried in air. Yield = 260 mg. (95%); m.p. 310° C. (dec.)

Workup

  1. customA clear solution formed
  2. waitfollowed, after a few minutes, by formation of a precipitate
  3. temperatureThe bomb is then cooled to room temperature
  4. customthe contents removed
  5. washThe bomb is washed with ethanol
  6. customthe combined reaction mixture
  7. washwash
  8. filtrationfiltered
  9. customto recover the product
  10. washThe filter cake is washed with ethanol
  11. customdried in air

Sources & evidence

ORD record
ord-632cc5822cc042c6b91d305967cd64e4
Source dataset
uspto-grants-1977_03
Patent number
US04011324

Reaction notes

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