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

HRID 2253341Notes

Reaction equation

HRID 2253341 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-0f1add079c5348c09779b5e59713aa0b
Source dataset
uspto-grants-2008_01
Patent number
US07323570B2

Reaction notes

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