3-Nitrobenzaldehyde → 1-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-(3-nitro-benzylideneamino)-pyrrolidin-1-yl)-4-oxo-5-vinyl-3-quinolinecarboxylic acid

HRID 2258126Notes

Reaction equation

[NH2:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[N+:7]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O)([O-:9])=[O:8].C1N2CCN(CC2)C1.[CH:26]1([N:29]2[C:38]3[C:33](=[C:34]([CH:42]=[CH2:43])[C:35]([F:41])=[C:36](F)[C:37]=3[F:39])[C:32](=[O:44])[C:31]([C:45]([OH:47])=[O:46])=[CH:30]2)[CH2:28][CH2:27]1>C(#N)C.CN(C)C=O>[CH:26]1([N:29]2[C:38]3[C:33](=[C:34]([CH:42]=[CH2:43])[C:35]([F:41])=[C:36]([N:4]4[CH2:5][CH2:6][CH:2]([N:1]=[CH:13][C:12]5[CH:15]=[CH:16][CH:17]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=5)[CH2:3]4)[C:37]=3[F:39])[C:32](=[O:44])[C:31]([C:45]([OH:47])=[O:46])=[CH:30]2)[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.39% of 3-amino-pyrrolidine in 4 ml of acetonitrile is treated with a solution of 0.75 g of 3-nitrobenzaldehyde in 4 ml of acetonitrile. After 1 hour at room temperature, the reaction mixture is treated with a solution of 1 g of DABCO and 0.93 g of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acid in 4 ml of dimethylformamide. After 1 hour under reflux, the reaction mixture is cooled to 0° C. and the product is filtered off with suction and dried. 1.33 g of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-(3-nitro-benzylideneamino)-pyrrolidin-1-yl)-4-oxo-5-vinyl-3-quinolinecarboxylic acid are obtained.

Workup

temperatureAfter 1 hour under reflux
filtrationthe product is filtered off with suction
customdried

Sources & evidence

ORD record: ord-1a16e4d10a384296aca12290d345de41
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05659038

Reaction notes

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