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Dimethylformamide → [(6-Nitro-5-quinolinyl)amino]oxo-acetic acid ethyl ester

HRID 48232
Notes
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Reaction equation

HRID 48232 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(N([CH2:20][CH3:21])CC)C.CC[C:24]([C:26](Cl)=[O:27])=[O:25].CN(C)C=[O:32]>>[CH2:20]([O:32][C:24](=[O:25])[C:26]([NH:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)=[O:27])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 1189016-Nitroquinolin-5-ylamineHCID 11007880Butanoyl chloride, 2-oxo-

Product 1

HCID 10085554[(6-Nitro-5-quinolinyl)amino]oxo-acetic acid ethyl esterYield 80%

Conditions

Temperature
50 °C

Procedure

A solution of 5-amino-6-nitroquinoline (3 g, 16 mmol) in 50 mL dimethylformamide was treated with triethylamine (3.2 g, 32 mmol) and ethyloxalyl chloride (3.2 g, 24 mmol) and heated at 50° C. for 1 hour. After removing the triethylamine hydrochloride by filtration, the filtrate was concentrated and diethyl ether added. The title compound (3.7 g, 80% yield) was collected by filtration.

Workup

  1. customAfter removing the triethylamine hydrochloride
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated
  4. additiondiethyl ether added

Sources & evidence

ORD record
ord-a11dfcfbd646463ca3727e7a64b8193d
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06703391B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes