Hydrochloric Acid → Ethyl 1-cyclopropyl-8-(difluoromethoxy)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
Reaction equation
[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:26])[C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([O:21][CH:22]([F:24])[F:23])[C:14]=2F)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[H-].[Na+].Cl>C(OCC)C>[CH:1]1([N:4]2[C:14]3[C:13](=[CH:18][C:17]([F:19])=[C:16]([F:20])[C:15]=3[O:21][CH:22]([F:24])[F:23])[C:12](=[O:26])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5]2)[CH2:3][CH2:2]1Participants
Procedure
The whole of the ethyl 3-cyclopropylamino-2-(3-difluoromethoxy-2,4,5-trifluorobenzoyl)acrylate [(XIX), R1 =--OCHF2, R3' =H, R17 =C2H5, X=X'=F] [prepared as described in step (c) above] was dissolved in 150 ml of anhydrous diethyl ether, and then 0.39 g (0.0098 moles) of a 60% w/w suspension of sodium hydride in mineral oil was added in portions, whilst stirring at room temperature, to the resulting solution. After completion of the addition, the stirring was continued at room temperature for an additional 1 hour, and then the mixture was acidified by the addition of 1N aqueous hydrochloric acid with vigorous stirring. The reaction mixture was filtered and washed with water and with diethyl ether, in that order, to give 1.44 g of ethyl 1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate as colorless needles, melting at 224°-226° C.
Workup
- additionwas added in portions
- additionAfter completion of the addition
- filtrationThe reaction mixture was filtered
- washwashed with water and with diethyl ether, in that order
Sources & evidence
- ORD record
- ord-9fd4d6a82bcf4ea8a37c098cfb007d7c
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05073556
Reaction notes
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