Formic Acid → Ethyl 6,7-difluoro-1-(formylamino)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate
Reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][N:12]1[C:21]2[C:16](=[CH:17][C:18]([F:25])=[C:19]([F:24])[C:20]=2[O:22][CH3:23])[C:15](=[O:26])[C:14]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:13]1>>[F:25][C:18]1[CH:17]=[C:16]2[C:21](=[C:20]([O:22][CH3:23])[C:19]=1[F:24])[N:12]([NH:11][CH:1]=[O:2])[CH:13]=[C:14]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:15]2=[O:26]Participants
Procedure
A solution was prepared by dropping 1.5 ml (0.04 mole) of formic acid onto 3.8 ml (0.04 mole) of acetic anhydride, whilst ice-cooling, and then stirring the mixture at the same temperature for 15 minutes and then at 50° C. for 15 minutes. This solution was added dropwise to a solution of 0.6 g (0.002 mole) of ethyl 1-amino-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (XV) [prepared as described in Step (D1) above] dissolved in 4.2 ml (0.11 mole) of formic acid, whilst ice-cooling. The mixture was stirred at room temperature for 9 hours. At the end of this time, the solvent was distilled off under reduced pressure from the mixture. The residue was washed, in turn, with water and diethyl ether, to give 0.6 g of ethyl 6,7-difluoro-1-(formylamino)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (XVI) as a pale yellow powder.
Workup
- customA solution was prepared
- temperaturewhilst ice-cooling
- waitat 50° C. for 15 minutes
- temperaturecooling
- stirringThe mixture was stirred at room temperature for 9 hours
- distillationAt the end of this time, the solvent was distilled off under reduced pressure from the mixture
- washThe residue was washed, in turn, with water and diethyl ether
Sources & evidence
- ORD record
- ord-86cc8adda0324853a407d49830b2b0e0
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04997943
Reaction notes
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