1,2-Dichloroethane → HCID 86680435, compound

HRID 1023197Notes

Reaction equation

HRID 1023197 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[O:27]=[C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:38][CH2:39][C:40]([NH:42][NH2:43])=[O:41])[CH:34]=2)[NH:29]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:43][NH:42][C:40](=[O:41])[CH2:39][O:38][C:33]2[CH:34]=[C:35]3[C:30](=[CH:31][CH:32]=2)[NH:29][C:28](=[O:27])[CH:37]=[CH:36]3)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 798743,4-Dichlorophenylacetic acidHCID 86680404HCID 86680404, compound

Product 1

HCID 86680435HCID 86680435, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(3,4-dichlorophenyl)acetic acid (0.440 g, 2.144 mmol) in DMF (15 mL), EDC (0.616 g, 3.22 mmol) and HOBT (0.328 g, 2.144 mmol) were added. The reaction mixture was stirred at room temperature for 10 min. To this suspension was added 2-((2-oxo-1,2-dihydroquinolin-6-yl)oxy)acetohydrazide (0.5 g, 2.144 mmol) and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated and ice cold water was added and stirred for 10 min. The solid which separated was filtered, washed with water, and dried to afford crude 2-(3,4-dichlorophenyl)-N′-(2-((2-oxo-1,2-dihydroquinolin-6-yl)oxy)acetyl)acetohydrazide as a brown solid (0.7 g, 78%). LCMS: RT 1.581 min. LCMS (ES-API), m/z 420.0 (M+H).

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. additionice cold water was added
  4. stirringstirred for 10 min
  5. customThe solid which separated
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-734fd4f836414f8fa369296d1a4f64bd
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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