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

HRID 344905Notes

Reaction equation

HRID 344905 reaction equation
[CH2:1](N)C.Cl[C:5]1[C:14]([C:15]([C:17](=[CH:23][N:24](C)[CH3:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])=[CH:13][C:12]2[C:7](=[CH:8][C:9]([F:28])=[C:10]([F:27])[CH:11]=2)[N:6]=1>C(O)C>[CH2:21]([O:20][C:18]([C:17]1[C:15](=[O:16])[C:14]2[CH:13]=[C:12]3[CH:11]=[C:10]([F:27])[C:9]([F:28])=[CH:8][C:7]3=[N:6][C:5]=2[N:24]([CH2:25][CH3:1])[CH:23]=1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 53731972Ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate

Product 1

HCID 194236943-Ethoxycarbonyl-7,8-difluoro-1-ethyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution at approximately 2° C. of ethylamine (14.6 g) in ethanol (200 cc) is added in the course of 10 minutes at between 2° and 5° C. and with stirring to a suspension of ethyl 2-(2-chloro-6,7-difluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (20 g) in ethanol (200 cc) at approximately 2° C., the mixture is stirred for a further 40 minutes at between 2° and 5° C. and the temperature is then allowed to rise to approximately 20° C. in the course of 2 hours. After 24 hours at approximately 20° C., the insoluble matter is drained and washed with ethanol (2×30 cc) and isopropyl ether (2×50 cc). 3-Ethoxycarbonyl-1-ethyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine (16.35 g) is obtained in the form of a beige solid, m.p. 290° C.

Workup

  1. customto rise to approximately 20° C. in the course of 2 hours
  2. waitAfter 24 hours at approximately 20° C.
  3. washwashed with ethanol (2×30 cc) and isopropyl ether (2×50 cc)

Sources & evidence

ORD record
ord-662a461c7afd46cfa73a17ddc7c1d5f4
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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