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

HRID 1073597Notes

Reaction equation

HRID 1073597 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 about 2° C., of 14.6 g of ethylamine in 200 cm3 of ethanol is added in the course of 10 minutes, at between 2° and 5° C., with stirring, to a suspension of 20 g of ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate in 200 cm3 of ethanol at about 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 about 20° C. in the course of 2 hours. After 24 hours at about 20° C., the insoluble matter is drained and washed with 2 times 30 cm3 of ethanol and 2 times 50 cm3 of diisopropyl ether. 16.35 g of 3-ethoxycarbonyl-1-ethyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthridine are obtained in the form of a beige solid melting at 290° C.

Workup

  1. customto rise to about 20° C. in the course of 2 hours
  2. waitAfter 24 hours at about 20° C.
  3. washwashed with 2 times 30 cm3 of ethanol and 2 times 50 cm3 of diisopropyl ether

Sources & evidence

ORD record
ord-32c7edb62bbd4c1a8c657ec94efe8f6d
Source dataset
uspto-grants-1990_11
Patent number
US04970213

Reaction notes

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