Ethanamine, 2-fluoro-, hydrochloride → HCID 20063282, compound

HRID 1084383Notes

Reaction equation

Cl.[F:2][CH2:3][CH2:4][NH2:5].Cl[C:7]1[C:16]([C:17]([C:19](=[CH:25]N(C)C)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:18])=[CH:15][C:14]2[C:9](=[CH:10][C:11]([Cl:30])=[C:12]([F:29])[CH:13]=2)[N:8]=1>C(N(CC)CC)C>[Cl:30][C:11]1[C:12]([F:29])=[CH:13][C:14]2[C:9]([CH:10]=1)=[N:8][C:7]1[N:5]([CH2:4][CH2:3][F:2])[CH:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:17](=[O:18])[C:16]=1[CH:15]=2

Participants

Conditions

Temperature: 75 °C

Procedure

2.7 cm3 of triethylamine are added to a suspension of 1.9 g of 2-fluoroethylamine hydrochloride in 25 cm3 of trichlorcmethane. 3.5 g of ethyl 2-(2,7-dichloro-6-fluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate are added to the solution obtained at about 20° C. After stirring at this temperature for 16 hours, the solution is concentrated to dryness under reduced pressure (20 kPa) at about 50° C. The residue is taken up in 20 cm3 of ethanol and 3 cm3 of triethylamine and heat at about 75° C., with stirring, for 2 hours. After cooling to about 20° C. the insoluble matter is drained and washed with twice 10 cm3 of ethanol and twice 10 cm3 of diisopropyl ether. 1.9 g of 8-chloro-3-ethoxycarbonyl-7-fluoro-1-(2-fluoro-ethyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine are obtained in the form of a yellow solid melting at 268° C., which is used for the subsequent steps without further purification.

Workup

customobtained at about 20° C
concentrationthe solution is concentrated to dryness under reduced pressure (20 kPa) at about 50° C
stirringwith stirring, for 2 hours
temperatureAfter cooling to about 20° C. the insoluble matter
washwashed with twice 10 cm3 of ethanol and twice 10 cm3 of diisopropyl ether

Sources & evidence

ORD record: ord-1914ae721aa34f7d84c6438af1b0afd0
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05004745

Reaction notes

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