Dimethylformamide → 1,4-Dihydro-4-oxo-8-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acid

HRID 851007

Reaction equation

HRID 851007 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][CH2:3]1.S(Cl)(Cl)=O.CN(C)C=O.[NH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[NH:28][CH:27]=[C:26]([C:30]([OH:32])=[O:31])[C:25]2=[O:33].C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl>[O:33]=[C:25]1[C:24]2[C: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][CH:23]=2)[NH:28][CH:27]=[C:26]1[C:30]([OH:32])=[O:31]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 7405L-Pyroglutamic AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 128663498-Amino-4-hydroxyquinoline-3-carboxylic acid

Product 1

HCID 131368721,4-Dihydro-4-oxo-8-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acidYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3.87 g (30 mmol) of 5-oxo-L-proline, 2.19 ml (30 mmol) of thionyl chloride, 2.32 ml (30 mmol) of dimethylformamide, and 75 ml of dichloromethane is stirred with cooling for 1 hour. A mixture of 4.08 g (20 mmol) 8-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 8.4 ml (60 mmol) of triethylamine, 7.6 ml (60 mmol) of chlorotrimethylsilane, and 100 ml of dichloromethane is stirred at room temperature for 40 minutes and then is cooled to 0°. The cold acid chloride solution is added to the cold silylated quinoline and the mixture is stirred with cooling for 4 hours and at room temperature overnight. The reaction mixture is evaporated to dryness and the residue is treated with ethanol to give 3.40 g of 1,4-dihydro-4-oxo-8-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acid.

Workup

  1. temperaturewith cooling for 1 hour
  2. stirringis stirred at room temperature for 40 minutes
  3. temperatureis cooled to 0°
  4. stirringthe mixture is stirred
  5. customThe reaction mixture is evaporated to dryness
  6. additionthe residue is treated with ethanol

Sources & evidence

ORD record
ord-bbb0dffa458949ceaefef443213fc58e
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Linked notes

Loading…