1,2-Dichloroethane → HCID 85717355, compound

HRID 1813873Notes

Reaction equation

HRID 1813873 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>[CH:10]1[C:5]2[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:3]=[C:2]([C:11]([O:13][N:19]2[C:23](=[O:24])[CH2:22][CH2:21][C:20]2=[O:25])=[O:12])[N:1]=1

Participants

6

Reactant 4

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

Product 1

HCID 85717355HCID 85717355, compound

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-a5acf6051b254fa5acd64af2c0df3a08
Source dataset
uspto-grants-2005_04
Patent number
US06875743B1

Reaction notes

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