Methylamine → 3-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 344871Notes

Reaction equation

HRID 344871 reaction equation
CN.Cl[C:4]1[C:13]([C:14]([C:16](=[CH:22][N:23](C)[CH3:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([F:27])=[C:9]([F:26])[CH:10]=2)[N:5]=1>C(O)C>[CH2:20]([O:19][C:17]([C:16]1[C:14](=[O:15])[C:13]2[CH:12]=[C:11]3[CH:10]=[C:9]([F:26])[C:8]([F:27])=[CH:7][C:6]3=[N:5][C:4]=2[N:23]([CH3:24])[CH:22]=1)=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 53731972HCID 53731972, compound

Product 1

HCID 98399873-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of methylamine (11.3 g) at approximately 0° C. in ethanol (50 cc) is added in the course of 10 minutes at between 0° and 5° C. to a stirred suspension, maintained at a temperature in the region of 0° C., of ethyl 2-(2-chloro-6,7-difluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (22.3 g) in ethanol (480 cc), the mixture is stirred for 1 hour at between 0° and 5° C., the temperature is allowed to rise to approximately 25° C. and the mixture is stirred for a further 16 hours at the same temperature. The insoluble matter is drained and washed with ethanol (3×100 cc) and ethyl ether (2×100 cc). After 1 recrystallization in dimethylformamide (250 cc), 3-ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (16 g) is obtained in the form of a yellow solid, m.p. 323° -324° C.

Workup

  1. customto rise to approximately 25° C.
  2. stirringthe mixture is stirred for a further 16 hours at the same temperature
  3. washwashed with ethanol (3×100 cc) and ethyl ether (2×100 cc)
  4. customAfter 1 recrystallization in dimethylformamide (250 cc)

Sources & evidence

ORD record
ord-8c9760d59d9747c29ff6c60e31813d50
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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