Water → HCID 11976497, compound

HRID 736446Notes

Reaction equation

HRID 736446 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1.ClC1C(Cl)=CC=CN=1.[OH2:21]>Cl>[Cl:1][C:2]1[C:3]([C:8]([CH3:12])([CH3:11])[C:9]([NH2:10])=[O:21])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 169882,3-DichloropyridineHCID 11976439HCID 11976439, compound

Product 1

HCID 11976497HCID 11976497, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
92.5 °C

Procedure

A crude mixture of 2-(3-chloropyridin-2-yl)-2-methylpropionitrile and 2,3-dichloropyridine (0.171 g) was dissolved in concentrated hydrochloric acid (4 mL) and the solution was heated to 90-95° C. for 5.5 hours. Upon cooling, it was diluted with water and extracted twice with dichloromethane. The aqueous phase was basified with sodium hydroxide (with cooling) to pH of 8 and extracted twice with dichloromethane. The organic extracts were washed with water and dried over anhydrous magnesium sulfate. Filtration and evaporation gave 2-(3-chloropyridin-2-yl)isobutyramide (64 mg). 1H-NMR (DMSO-d6): δ 8.48 (dd, 4.6, 1.5 Hz), 7.83 (dd, 7.95, 1.5), 7.325 (dd, 7.95, 4.6), 6.97 and 6.93 (2 s, CONH2), 1.50 (s, 6H).

Workup

  1. temperatureUpon cooling
  2. extractionextracted twice with dichloromethane
  3. extractionextracted twice with dichloromethane
  4. washThe organic extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-adbfadce431749b9b4af6e93729ee05a
Source dataset
uspto-grants-2009_09
Patent number
US07595338B2

Reaction notes

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