Ethanol → Ethyl 7-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 1461389Notes

Reaction equation

[N:1]([C:4]1[C:13]([F:14])=[C:12]2[C:7]([C:8](=[O:23])[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:10][N:11]2[CH:15]2[CH2:17][CH2:16]2)=[CH:6][C:5]=1[F:24])=[N+]=[N-].C(O)C>CN(C)C=O.[Pd]>[NH2:1][C:4]1[C:13]([F:14])=[C:12]2[C:7]([C:8](=[O:23])[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:10][N:11]2[CH:15]2[CH2:17][CH2:16]2)=[CH:6][C:5]=1[F:24]

Participants

Conditions

Temperature: 5 °C

Procedure

A slurry of 1.20 kg of ethyl 7-azido-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 12 L of dimethylformamide was charged to a five gallon autoclave. After placing the vessel under nitrogen, a slurry of 76 g of 10% palladium-on-carbon in 700 ml of dimethylformamide was added. The mixture was hydrogenated at 48-50 p.s.i. and 600 r.p.m. for four hours. The reaction mixture was filtered and concentrated under aspirator pressure to give a thick but stirrable dark residue. Ethanol (3 L) was added and the suspension was briefly refluxed before allowing to cool. After cooling to 5° C., the product was collected, washed with 2×500 ml of cold ethanol and then dried at 65°-70° C. in vacuo overnight to give 962 g (86.7%) of product.

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated under aspirator pressure
customto give a thick but stirrable dark residue
temperaturethe suspension was briefly refluxed
temperatureto cool
customthe product was collected
washwashed with 2×500 ml of cold ethanol
customdried at 65°-70° C. in vacuo overnight

Sources & evidence

ORD record: ord-8cb124bfe77844faa1e40be962e9b03d
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075319

Reaction notes

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