Hydrazine hydrate (1:1) → HCID 178509288, compound

HRID 510434Notes

Reaction equation

HRID 510434 reaction equation
[C:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[Cl:17])[C:4](OCC)=O)#[N:2].[OH2:18].[NH2:19][NH2:20]>C(O)C>[NH2:2][C:1]1[C:3]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=2[Cl:17])=[C:4]([OH:18])[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 71270754Ethyl 2-cyano-3-(2,3-dichlorophenyl)propanoate

Product 1

HCID 178509288HCID 178509288, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-cyano-3-(2,3-dichlorophenyl)propanoate (30 g, 0.11 mol) and hydrazine hydrate (11 g, 0.22 mol) in ethanol (300 mL), was stirred under reflux for 16 h. The reaction mixture was cooled and filtered to provide the titled compound (19 g) and the filtrate was concentrated to provide the crude titled compound (18 g); LC/MS: MS (ES+) m/e 258 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.47 (s, 2H), 4.12 (s, 2H), 7.02 (dd, J=1.5, 7.8 Hz, 1H), 7.23 (t, J=7.8 Hz, 1H), 7.36 (s, 1H), 7.44 (dd, J=1.5, 7.8 Hz, 1H), 9.06 (s, 1H).

Workup

  1. temperatureunder reflux for 16 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ca74a468007542dbac0ccbaad1535407
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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