Water → 3-Chloro-4-(methylamino)benzonitrile

HRID 1348907Notes

Reaction equation

HRID 1348907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[CH3:11][NH2:12].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:12][CH3:11])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 1455253-Chloro-4-fluorobenzonitrile

Product 1

HCID 159077543-Chloro-4-(methylamino)benzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-chloro-4-fluorobenzonitrile (5.2 g, 33 mmol), THF (55 mL), and 40% methylamine in water (25 mL, 290 mmol) in a sealed tube was heated to 65° C. for 1.5 hours, cooled to room temperature. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The resulting solid was dried for about 16 hours under high vacuum in the presence of P2O5 to provide 6.3 g (95%) of the desired product. MS (DCI/NH3) m/z 184, 186 (M+H+NH3)+; 1H NMR (DMSO-d6) δ 7.72 (d, 1H), 7.55 (dd, 1H), 6.70 (d, 1H), 6.52 (br q, 1H), 2.80 (d, 3H).

Workup

  1. temperaturecooled to room temperature
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dry with materialThe resulting solid was dried for about 16 hours under high vacuum in the presence of P2O5

Sources & evidence

ORD record
ord-45fc71d0235945cebc01eed26239e3a8
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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