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

HRID 1112252Notes

Reaction equation

HRID 1112252 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-dimethoxypyrimido[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-8b380fc898e14cdd865e4e87d634de72
Source dataset
uspto-grants-1978_10
Patent number
US04120962

Reaction notes

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