2-Amino-4-nitrobenzonitrile → 2-(Aminomethyl)-5-nitroaniline

HRID 1688133Notes

Reaction equation

HRID 1688133 reaction equation
CSC.B.[NH2:5][C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]>C1COCC1>[NH2:9][CH2:8][C:7]1[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:6]=1[NH2:5]

Participants

4

Reactant 2

HCID 111478972-Amino-4-nitrobenzonitrileHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 578538082-(Aminomethyl)-5-nitroanilineYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethyl sulfide (40 mL, 80 mmol) was added dropwise to a stirring solution of 2-amino-4-nitro-benzonitrile (2.27 g, 14 mmol) in dry THF (50 mL) at room temperature. The mixture was stirred at same temperature for 3 hours, and then carefully quenched with 1N aqueous HCl. The mixture was made basic (pH>11) with 4N sodium hydroxide and extracted with methylene chloride. The organic phase was dried over sodium sulfate, filtered and concentrated to provide 1.75 g of 2-aminomethyl-5-nitro-phenylamine (75%): 1H NMR (300 MHz, CDCl3) δ7.6 (m, 2H), 7.25 (d, 1H), 5.1 (br, 2H), 4.1 (s, 3H); MS (m/e): 168.1 (M+1).

Workup

  1. customcarefully quenched with 1N aqueous HCl
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31568975d2d54bbe8e81ce9239b85f87
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…