HCID 59002907, compound → HCID 59002870, compound

HRID 561157Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N+:24]([O-])=O)=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[N:8]([CH:15]1[CH2:17][CH2:16]1)[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23]>CC(O)=O.[Fe]>[NH2:24][C:3]1[C:2]([Cl:1])=[C:11]([F:12])[C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[C:5](=[O:23])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][N:8]2[CH:15]1[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 6-chloro-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (240 mg, 0.624 mmol) and iron powder (209 mg, 3.74 mmol) in AcOH (10 mL) was stirred at 90° C. for 6 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. After water was added, the crude product was extracted with EtOAc, washed successively with saturated aq. NaHCO3 and brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.) Hexane:EtOAc 5:1→1:1) to yield ethyl 5-amino-6-chloro-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (141 mg, 64%) as a colorless solid.

Workup

customThe catalyst was removed by filtration over Celite
concentrationthe filtrate was concentrated in vacuo
additionAfter water was added
extractionthe crude product was extracted with EtOAc
washwashed successively with saturated aq. NaHCO3 and brine
dry with materialdried over MgSO4
customthe solvent was removed in vacuo
customThe crude product was purified by column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.) Hexane:EtOAc 5:1→1:1)

Sources & evidence

ORD record: ord-8374014b801b40c2ab199213cbb86c04
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063221B2

Reaction notes

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