Dimethylformamide → 1,4-Dihydro-4-oxo-7-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acid
Reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][CH2:3]1.CN(C)C=O.S(Cl)(Cl)=O.[NH2:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24](=[O:33])[C:25]([C:30]([OH:32])=[O:31])=[CH:26][NH:27]2)=[CH:22][CH:21]=1.C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl>[O:33]=[C:24]1[C:23]2[C:28](=[CH:29][C:20]([NH:19][C:7]([CH:5]3[CH2:4][CH2:3][C:2](=[O:1])[NH:6]3)=[O:9])=[CH:21][CH:22]=2)[NH:27][CH:26]=[C:25]1[C:30]([OH:32])=[O:31]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 3.87 g (30 mmol) of 5-oxo-L-proline, 2.32 ml (30 mmol) of dimethylformamide, 2.19 ml (30 mmol) of thionyl chloride, and 75 ml of dichloromethane is stirred with cooling for 50 minutes. A mixture of 4.08 g (20 mmol) of 7-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 8.4 ml (60 mmol) of triethylamine, 7.6 ml (60 mmol) of chlorotrimethylsilane, and 200 ml of dichloromethane is stirred at room temperature for 50 minutes and then cooled to 0° C. The cold acid chloride solution is added to the cold silylated quinoline and is stirred with cooling for 3 hours and at room temperature overnight. The reaction mixture is evaporated to dryness and the residue is treated with water and ethanol. The solid is filtered to give 4.72 g of 1,4-dihydro-4-oxo-7-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acid.
Workup
- temperaturewith cooling for 50 minutes
- stirringis stirred at room temperature for 50 minutes
- stirringis stirred
- temperaturewith cooling for 3 hours and at room temperature overnight
- customThe reaction mixture is evaporated to dryness
- additionthe residue is treated with water and ethanol
- filtrationThe solid is filtered
Sources & evidence
- ORD record
- ord-792583580aa74d08b6f51429eaf53be9
- Source dataset
- uspto-grants-1983_09
- Patent number
- US04404201
Reaction notes
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