Ammonia → 2-Amino-3-chloro-6-fluorobenzonitrile

HRID 1418361Notes

Reaction equation

HRID 1418361 reaction equation
[NH3:1].[Cl:2][C:3]1[C:4](F)=[C:5]([C:8]([F:11])=[CH:9][CH:10]=1)[C:6]#[N:7]>C(#N)C>[NH2:1][C:4]1[C:3]([Cl:2])=[CH:10][CH:9]=[C:8]([F:11])[C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 131752313-Chloro-2,6-difluorobenzonitrile

Product 1

HCID 539633822-Amino-3-chloro-6-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Aqueous ammonia (d 0.880, 2 ml) was added to a solution of 3-chloro-2,6-difluorobenzonitrile (1.93 g, 11.1 mmol) in acetonitrile (10 ml), and the mixture heated to 60° C. for 16 h. The resulting brown solution was evaporated and purified by flash chromatography eluting with 5% ethyl acetate/hexane, increasing the gradient to 20% ethyl acetate/hexane, to furnish a white solid (410 mg), MS (+EI) 173/171 (M+); 1H NMR (CDCl3) 7.39 (1H, dd, J5.7, 9.0 Hz), 6.46 (1H, t, J8.7 Hz), 4.95 (2H, br. s).

Workup

  1. customThe resulting brown solution was evaporated
  2. custompurified by flash chromatography
  3. washeluting with 5% ethyl acetate/hexane
  4. temperatureincreasing the gradient to 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d61ca91cb2c24af7af1640708fd82a99
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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