Water → 6-Chloro-3-pyridinecarbonitrile

HRID 2210667Notes

Reaction equation

HRID 2210667 reaction equation
CN(C)[CH:3]=[CH:4][C:5]#N.[CH3:8][N:9]([CH:11]=O)C.[ClH:13].O.C[N:16]([CH:18]=O)C>Cl>[Cl:13][C:8]1[CH:5]=[CH:4][C:3]([C:18]#[N:16])=[CH:11][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 974973-(Dimethylamino)prop-2-enenitrileHCID 10920465N,N-dimethylformamide;hydrochloride

Product 1

HCID 51520946-Chloro-3-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

13.2 g of β-dimethylamino-acrylonitrile were added dropwise at 30° C. to a solution of 22 g of DMF/HCl adduct in 100 ml of DMF. Following an after-reaction time of 2 h, this solution was added dropwise, while passing in HCl, to a solution, saturated at 50° C., of HCl gas in DMF. The temperature was maintained at 50° C. by cooling. After conventional work up (40 ml of water), 2-chloro-5-cyanopyridine was obtained in 77.7% of the theoretical yield, based on the C3 unit employed.

Workup

  1. customan after-reaction time of 2 h
  2. additionthis solution was added dropwise
  3. temperatureby cooling

Sources & evidence

ORD record
ord-20671d93940e49bb80b122da984391f3
Source dataset
uspto-grants-1995_10
Patent number
US05459273

Reaction notes

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