Water → 2-(2,4-Dichloro-phenyl)-3-(6-methoxy-pyridin-3-yl)-3-oxo-propionitrile

HRID 1097964Notes

Reaction equation

HRID 1097964 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[N:6][CH:5]=1.[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[CH2:16][C:17]#[N:18].O>C(O)(C)(C)C>[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[CH:16]([C:3]([C:4]1[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)=[O:12])[C:17]#[N:18]

Participants

5

Reactant 3

HCID 962WaterHCID 805662,4-DichlorophenylacetonitrileHCID 586039Methyl 6-methoxypyridine-3-carboxylate

Product 1

HCID 668131162-(2,4-Dichloro-phenyl)-3-(6-methoxy-pyridin-3-yl)-3-oxo-propionitrileYield 29.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of potassium-tert-butylate (2.052 g) in tert-butanol (25 ml) was added methyl-6-methoxynicotinate (2.5 g). 2,4-Dichlorobenzyl cyanide (2.782 g) was added potion wise. The mixture was heated to 100° C. for 1.5 h. After cooling to room temperature, water (100 ml) was added and the mixture was washed with diethyl ether. The aqueous phase was neutralized with concentrated aqueous HCl and extracted with EtOAc. The organic phase was washed with water and with brine, dried (MgSO4), filtered and concentrated to dryness to give the title compound (1.407 g) as a yellow foam that was used in the next step without further purification. MS (m/e)=321.0 [M+H+].

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe mixture was washed with diethyl ether
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water and with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-537dcb9a09544232a9949c561367cdbc
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

Loading…