4-Amino-2-fluoro-5-nitrobenzonitrile → 4,5-DiaMino-2-fluorobenzonitrile

HRID 1858011Notes

Reaction equation

HRID 1858011 reaction equation
[NH2:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:13])[CH:3]=1>O=[Pt]=O.CO>[NH2:1][C:2]1[C:9]([NH2:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:13])[CH:3]=1

Participants

4

Reactant 1

HCID 104197934-Amino-2-fluoro-5-nitrobenzonitrile

Product 1

HCID 221255144,5-DiaMino-2-fluorobenzonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture comprising 2,4-difluoro-5-nitrobenzonitrile (9.03 g, 0.049 mol) and ethanol (10-15 mL) was stirred at ambient temperature while concentrated ammonium hydroxide (40 mL) was slowly added to give a precipitate. The precipitate was isolated by filtration and lyophilized to give 4-amino-2-fluoro-5-nitrobenzonitrile (7.84 g, 0.043 mol) as an off-white solid; PB-CI/MS: 182=(MH+); 1H-NMR (300 Mhz, DMSO-d6): 6.856(d, 1H), 8.22(bs, 2H), 8.577(d, 1H). A mixture of 4-amino-2-fluoro-5-nitrobenzonitrile (3 g, 0.017 mol), PtO2 (≈300 mg) and methanol (20 mL)was hydrogenated (1 atm) for approximately 12 hours, filtered over celite and concentrated to dryness to provide 4,5-diamino-2-fluorobenzonitrile (2.5 g, 0.017 mol) as a brown solid PB-CI/MS: 152=(MH+); 1H-NMR (300 Mhz, DMSO-d6): 4.7(bs, 2H), 5.863(bs, 2H), 6.375(d, 1H), 6.56(d, 1H).

Workup

  1. customfor approximately 12 hours
  2. filtrationfiltered over celite and
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-af859fe54a11492c8c7308a21b77ad97
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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