Ethyl isocyanate → 6-[[(Ethylamino)carbonyl]-amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1758487

Reaction equation

HRID 1758487 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]([C:12]([OH:14])=[O:13])[C:5]2=[O:15].[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][CH:7]=[C:6]([C:12]([OH:14])=[O:13])[C:5]2=[O:15])=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 32812016-Amino-4-hydroxyquinoline-3-carboxylic acid

Product 1

HCID 131063376-[[(Ethylamino)carbonyl]-amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.08 g (20 mmol) of 6-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid [J. Pharm. Sci., 11, 1051 (1963)] 2.37 ml (30 mmol) of ethyl isocyanate, 2.8 ml (20 mmol) of triethylamine and 50 ml of dimethylformamide is stirred at room temperature overnight. The solution is evaporated to dryness and the residue is treated with 1 N hydrochloric acid. The solid is filtered to give 4.56 g of 6-[[(ethylamino)carbonyl]-amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp>320° C.

Workup

  1. customThe solution is evaporated to dryness
  2. additionthe residue is treated with 1 N hydrochloric acid
  3. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-19a0b53de0654a1690ffa7d0681a309a
Source dataset
uspto-grants-1983_02
Patent number
US04374138

Linked notes

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