Formamide → HCID 18426727, compound

HRID 380170Notes

Reaction equation

HRID 380170 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([C:23]([O:25]CC)=O)[C:6]1=[O:28])[CH2:2][CH2:3][CH3:4].C([NH2:31])=O.C[O-].[Na+].CO>O.CN(C)C=O>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([C:23](=[O:25])[NH2:31])[C:6]1=[O:28])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 713FormamideHCID 887MethanolHCID 10942334Sodium MethoxideHCID 18426713HCID 18426713, compound

Product 1

HCID 18426727HCID 18426727, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-butyl-3-ethoxycarbonyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine (45.0 g, 120 mmol), formamide (15.5 ml, 390 mmol) and dimethylformamide (120 ml) was dissolved at 60° C., and thereto was added a 25% solution of sodium methoxide in methanol (108 ml, 390 mmol), and the mixture was stirred at 60° C. for 9 hours. The mixture was cooled to 0° C., and thereto was added water (1.2 liter), and the mixture was stirred for 15 minutes. The precipitated solid was collected by filtration, washed with ethanol, and dried to give the title compound (37.8 g, yield; 87%) as white powder.

Workup

  1. dissolutionwas dissolved at 60° C.
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringthe mixture was stirred for 15 minutes
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-5b43af2fdffc42c98919258c5d7d2291
Source dataset
uspto-grants-2001_10
Patent number
US06300500B1

Reaction notes

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