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1,2-Dichloroethane → 1-((2-Quinolinyl-carbonyl)oxy)-2,5-pyrrolidinedione

HRID 1358188
Notes
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Reaction equation

HRID 1358188 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=[O:12].C(Cl)CCl.O[N:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25].C([O-])(O)=O.[Na+]>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([O:13][N:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25])=[O:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7124Quinaldic AcidHCID 80170N-HydroxysuccinimideHCID 516892Sodium Bicarbonate

Product 1

HCID 109236041-((2-Quinolinyl-carbonyl)oxy)-2,5-pyrrolidinedione

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-quinoline carboxylic acid (1.2 eq.) in DMF at 0° C. was treated with EDC (1.4 eq.). The mixture was stirred at 0° C. for 1 to 2 h and then N-hydroxysuccinimide (1.0 eq.) was added. After stirring at RT for more than 3 h, the reaction mixture was poured into 60% sat. NaHCO3 and the product filtered: 1H NMR (CDCl3, 300 MHz, ppm) 8.35 (d, 1H), 8.27 (d, 1H), 8.19 (d, 1H), 7.87 (d, 1H), 7.80 (m, 1H), 7.68 (m, 1H), 2.91 (s, 4H).

Workup

  1. stirringAfter stirring at RT for more than 3 h
  2. filtrationthe product filtered

Sources & evidence

ORD record
ord-6e27b028aaba4823ba173790e6a8fba3
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06596687B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes