Ethyl isocyanate → 6-[[(Ethylamino)carbonyl]amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid

HRID 1758485Notes

Reaction equation

HRID 1758485 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]([OH:15])=[O:14])=[CH:5]2.[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17].C(N(CC)CC)C>CN(C)C=O>[CH2:16]([NH:18][C:19]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]([OH:15])=[O:14])=[CH:5]2)=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 131063306-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Product 1

HCID 205093946-[[(Ethylamino)carbonyl]amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.08 g (20 mmol) of 6-amino-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, 2.37 ml (30 mmol) of ethyl isocyanate, 2.8 ml (20 mmol) of triethylamine and 50 ml of dimethylformamide is stirred with ice bath cooling for 4.5 hrs. The reaction solution is evaporated to dryness and is treated with 1 N hydrochloric acid and ethanol to yield 5.12 g of 6-[[(ethylamino)carbonyl]amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid.

Workup

  1. temperaturecooling for 4.5 hrs
  2. customThe reaction solution is evaporated to dryness
  3. additionis treated with 1 N hydrochloric acid and ethanol

Sources & evidence

ORD record
ord-ba06a6fcf0a248d09451586b186ec9ee
Source dataset
uspto-grants-1983_02
Patent number
US04374138

Reaction notes

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