1,2-Dichloroethane → 1-[(Quinoline-2-carbonyl)oxy]pyrrolidine-2,5-dione

HRID 1978806Notes

Reaction equation

HRID 1978806 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]

Participants

6

Reactant 4

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

Product 1

HCID 109236041-[(Quinoline-2-carbonyl)oxy]pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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-30f939994622473485d23148a3464d78
Source dataset
uspto-grants-2001_05
Patent number
US06239108B1

Reaction notes

Loading…