Ammonia → 2-Amino-3,6-difluorobenzonitrile

HRID 1418359Notes

Reaction equation

HRID 1418359 reaction equation
F[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].O.[NH3:13]>C(#N)C>[NH2:13][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 1456222,3,6-Trifluorobenzonitrile

Product 1

HCID 450905912-Amino-3,6-difluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,3,6-Trifluorobenzonitrile (1.76 ml, 15.2 mmol) in aqueous ammonia (20 ml) and acetonitrile (10 ml) was stirred for 7 days. Water was added. The whole was extracted with ether, the ether was dried (sodium sulphate) and evaporated. Flash column chromatography on silica gel, eluting with dichloromethane, gave the product (1.2 g), MS (+EI) 154 (M+), 1H NMR (CDCl3) 7.07-7.16 (1H, m), 6.36-6.43 (1H, m), 4.62 (2H, s).

Workup

  1. extractionThe whole was extracted with ether
  2. dry with materialthe ether was dried (sodium sulphate)
  3. customevaporated
  4. washFlash column chromatography on silica gel, eluting with dichloromethane

Sources & evidence

ORD record
ord-d58cefe9ca844147a6bbb301c478e1e4
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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