Acetic Acid → HCID 23113351, compound

HRID 75509Notes

Reaction equation

HRID 75509 reaction equation
[C:1](O)(=O)C.[Cl:5][C:6]1[CH:11]=[C:10](OC)[CH:9]=[CH:8][C:7]=1[CH:14]([C:17](=O)[CH3:18])[C:15]#[N:16].[OH2:20].[NH2:21][NH2:22]>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[C:10]([O:20][CH3:1])[CH:9]=[CH:8][C:7]=1[C:14]1[C:15]([NH2:16])=[N:21][NH:22][C:17]=1[CH3:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 221781542-(2-Chloro-4-methoxyphenyl)-3-oxobutanenitrile

Product 1

HCID 23113351HCID 23113351, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetic acid (1.3 ml, 22.36 mmol) was added to a stirred suspension of 2-(2-chloro-4-methoxyphenyl)-3-oxobutanenitrile (2.0 g, 8.94 mmol) and hydrazine hydrate (0.65 ml, 13.41 mmol) in dry toluene (25 ml). The reaction mixture was heated at reflux for 20 h. The solvent was removed in vacuo and the residue was partitioned between 2M HCl and EtOAc. The organic extract was extracted several times with 2M HCl then discarded. The acidic extract was neutralised with NaHCO3 then re-extracted 3× with EtOAc. The combined organic extracts were dried (MgSO4) and the solvent removed to give the title compound as a viscous gum. No further purification was carried out; LCMS: Rt 1.19 mins; [M+H]+ 238.1 1H NMR (400 MHz, d6-DMSO) δ 1.95 (3H, s), 3.80 (3H, s), 4.1 (2H, br m), 6.92 (1H, s), 7.10 (1H, s), 7.20 (1H, d).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between 2M HCl and EtOAc
  5. extractionThe organic extract
  6. extractionwas extracted several times with 2M HCl
  7. extractionThe acidic extract
  8. extractionthen re-extracted 3× with EtOAc
  9. dry with materialThe combined organic extracts were dried (MgSO4)
  10. customthe solvent removed

Sources & evidence

ORD record
ord-5759e8e8560147679cbb1c6d4879eabf
Source dataset
uspto-grants-2014_09
Patent number
US08835444B2

Reaction notes

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