Dimethylformamide → 1,4-Dihydro-4-oxo-7-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acid

HRID 851004Notes

Reaction equation

HRID 851004 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.Cl[Si](C)(C)C>ClCCl.C(N(CC)CC)C>[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

8

Reactant 5

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 7405L-Pyroglutamic AcidHCID 24386Thionyl ChlorideHCID 102623227-Amino-4-hydroxyquinoline-3-carboxylic acid

Product 1

HCID 131368701,4-Dihydro-4-oxo-7-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acidYield 74.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

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, [J. Amer. Chem. Soc., 69, 371 (1947)], 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°. 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

  1. temperaturewith cooling for 50 minutes
  2. stirringis stirred at room temperature for 50 minutes
  3. temperaturecooled to 0°
  4. stirringis stirred
  5. customThe reaction mixture is evaporated to dryness
  6. additionthe residue is treated with water and ethanol
  7. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-934891fc8c89428fad461bff15396d24
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Reaction notes

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