Dimethylformamide → Ethyl 7-Chloropyrimido[4,5-b]quinolin-4(3H)-one-2-carboxylate

HRID 442209Notes

Reaction equation

HRID 442209 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:12])[C:6]([C:13]([NH2:15])=[O:14])=[CH:5]2.[H-].[Na+].CN(C)C=O.[C:23](OCC)(=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25]>O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]1[N:12]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[NH:15][C:13](=[O:14])[C:6]1=[CH:5]2

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 7268Diethyl OxalateHCID 24758Sodium hydride2×HCID 12594648HCID 12594648, compound

Product 1

HCID 135705337Ethyl 7-Chloropyrimido[4,5-b]quinolin-4(3H)-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 6-chloro-2-aminoquinoline-3-carboxamide (2.2 g., 0.01 mole), sodium hydride (0.52 g., 0.012 mole as 56% dispersion in oil) and N,N-dimethylformamide (20 ml.) is added to a solution of diethyl oxalate (5 ml.) and N,N-dimethylformamide (5 ml.). The reaction mixture is stirred for 15 minutes, a second portion of sodium hydride (0.52 g., 0.012 mole) added and stirring continued for an additional 15 minutes. Acetic acid (25.0 ml.) is cautiously added to the mixture followed by water (50 ml.). The tan precipitate is removed by filtration and dried (2.0 g. of crude ester). It is purified by chromatography on silica gel using chloroform: 2B ethanol (99:1) as eluant. The product, recovered by concentration of the eluate, is recrystallized from acetic acid. Yield = 1.3 g. (37.3%). M.P. 260.5° C. (dec.). Mass spectra gave m/e = 303.

Workup

  1. stirringstirring
  2. waitcontinued for an additional 15 minutes
  3. customThe tan precipitate is removed by filtration
  4. dry with materialdried (2.0 g. of crude ester)
  5. customIt is purified by chromatography on silica gel
  6. customThe product, recovered by concentration of the eluate,
  7. customis recrystallized from acetic acid
  8. customMass spectra gave m/e = 303

Sources & evidence

ORD record
ord-42cfa50c78b643c4811d3839cfad3773
Source dataset
uspto-grants-1977_08
Patent number
US04044134

Reaction notes

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