Dimethylformamide → 1,2-Dihydro-2-oxo-6-[(5-oxo-2-pyrrolidinyl)amino]3-quinolinecarboxylic acid

HRID 850997Notes

Reaction equation

HRID 850997 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5](C(O)=O)[CH2:4][CH2:3]1.CN(C)C=O.S(Cl)(Cl)=O.[NH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:30])[C:24]([C:31]([OH:33])=[O:32])=[CH:23]2.C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl>[O:30]=[C:25]1[C:24]([C:31]([OH:33])=[O:32])=[CH:23][C:22]2[C:27](=[CH:28][CH:29]=[C:20]([NH:19][CH:5]3[CH2:4][CH2:3][C:2](=[O:1])[NH:6]3)[CH:21]=2)[NH:26]1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 7405L-Pyroglutamic AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 131063306-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Product 1

HCID 205034311,2-Dihydro-2-oxo-6-[(5-oxo-2-pyrrolidinyl)amino]3-quinolinecarboxylic acidYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2.32 g (18 mmol) 5-oxo-L-proline, 1.39 ml (18 mmol) dimethylformamide, and 45 ml of dichloromethane is stirred at 0°-5° and 1.32 ml (18 mmol) of thionyl chloride is added. The reaction mixture is stirred at 0°-5° for 1 hour. A mixture of 2.45 g (12 mmol) of 6-amino-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, 100 ml of dichloromethane, 5.04 ml (36 mmol) triethylamine and 4.57 ml (36 mmol) chlorotrimethylsilane is stirred at room temperature for 40 min and then is cooled to 0°-5°. The solution of the acid chloride complex is added to the silylated quinoline acid and 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 methanol and filtered to give 2.1 g of 1,2-dihydro-2-oxo-6-[(5-oxo-2-pyrrolidinyl)amino]3-quinolinecarboxylic acid. mp>300°

Workup

  1. stirringThe reaction mixture is stirred at 0°-5° for 1 hour
  2. stirringis stirred at room temperature for 40 min
  3. temperatureis cooled to 0°-5°
  4. stirringis stirred
  5. customThe reaction mixture is evaporated to dryness
  6. additionthe residue is treated with methanol
  7. filtrationfiltered

Sources & evidence

ORD record
ord-a2a101d049fd4c85b9163cd68c75bc6b
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Reaction notes

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