Formamide → HCID 18426727, compound

HRID 1281246Notes

Reaction equation

HRID 1281246 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 to 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. customto dried

Sources & evidence

ORD record
ord-ae3510e92bc643868720d5fe3bfacfec
Source dataset
uspto-grants-2002_09
Patent number
US06452008B2

Reaction notes

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