Cyclopropylamine → 1-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 344908Notes

Reaction equation

Cl[C:2]1[C:11]([C:12]([C:14](=[CH:20][N:21](C)[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:25])=[C:7]([F:24])[CH:8]=2)[N:3]=1.[CH:26]1(N)C[CH2:27]1>ClC(Cl)Cl>[CH:22]1([N:21]2[C:2]3[N:3]=[C:4]4[CH:5]=[C:6]([F:25])[C:7]([F:24])=[CH:8][C:9]4=[CH:10][C:11]=3[C:12](=[O:13])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20]2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of ethyl 2-(2-chloro-6,7-difluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (20 g) and cyclopropylamine (9.25 g) in trichloromethane (80 cc) is stirred at a temperature in the region of 20° C. for 5 hours. The solution is concentrated under reduced pressure (20 kPa) at approximately 40° C. The residue is taken up in ethanol (300 cc), treated with DBU (8.2 g) and heated with stirring to approximately 75° C. for 30 minutes. After cooling to approximately 20° C., the insoluble matter is drained and washed with ethanol (2×30 cc). 1-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (11.1 g) is obtained in the form of a yellow solid, m.p. 230° C.

Workup

concentrationThe solution is concentrated under reduced pressure (20 kPa) at approximately 40° C
additiontreated with DBU (8.2 g)
temperatureheated
temperatureAfter cooling to approximately 20° C.
washwashed with ethanol (2×30 cc)

Sources & evidence

ORD record: ord-cec8941464424202b247355dcef85958
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Reaction notes

Loading…