Methylamine → N-Methyl-7,8-dimethoxypyrimido[4,5-b]quinolin-4(3H)-one-2-carboxamide

HRID 596597Notes

Reaction equation

HRID 596597 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])[N:9]=[C:8]1[N:15]=[C:16]([C:20]([O:22]CC)=O)[NH:17][C:18](=[O:19])[C:7]1=[CH:6]2.[CH3:25][NH2:26]>C(O)C>[CH3:25][NH:26][C:20]([C:16]1[NH:17][C:18](=[O:19])[C:7]2[C:8]([N:15]=1)=[N:9][C:10]1[C:5]([CH:6]=2)=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=1)=[O:22]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 135445830Pirolate

Product 1

HCID 135573285N-Methyl-7,8-dimethoxypyrimido[4,5-b]quinolin-4(3H)-one-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 7,8-dimethoxypyrimido[4,5-b]quinolin-4(3H)-one-2-carboxylate (300 mg., 0.90 mM) and ethanol (75 ml.) saturated with anhydrous monomethylamine is heated at 95° C. for 24 hours in a stainless steel bomb. The bomb and contents are cooled, the contents removed and concentrated to dryness under reduced pressure. The residue is recrystallized from chloroform/ethyl acetate to give 250 mg. (88%) of product, m.p. 334° C. (dec.).

Workup

  1. temperatureThe bomb and contents are cooled
  2. customthe contents removed
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue is recrystallized from chloroform/ethyl acetate
  5. customto give 250 mg

Sources & evidence

ORD record
ord-feeb0c2d82f3425980a742f878ff4a2b
Source dataset
uspto-grants-1977_03
Patent number
US04011324

Reaction notes

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