3-Methyl-4-nitrobenzonitrile → 4-Amino-3-methylbenzonitrile

HRID 1767007Notes

Reaction equation

HRID 1767007 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[C:5]#[N:6]>CC(O)=O.CCOC(C)=O.[Fe]>[NH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 1

HCID 28014343-Methyl-4-nitrobenzonitrile

Product 1

HCID 70103164-Amino-3-methylbenzonitrileYield 94.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methyl-4-nitro-benzonitrile (20 g, 0.123 mol) in HOAc (200 mL) was added iron powder (17.55 g, 0.309 mol). After 10 min, the reaction was exothermic and turned to dark color. The reaction mixture was allowed to stir at room temperature for 14 h and then diluted with EtOAc (200 mL). The brown precipitate was filtered through a pad of celite and the filtercake was rinsed with EtOAc. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (40% EtOAc/hexane) to yield the title compound (15.3 g, 92%). 1H NMR (300 MHz, CDCl3) δ 7.30-7.34 (2H, m), 6.64 (1H, d, J=8.7 Hz), 2.16 (3H, s). LCMS (M+H)+ m/z 133 (t=0.93 min).

Workup

  1. filtrationThe brown precipitate was filtered through a pad of celite
  2. washthe filtercake was rinsed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (40% EtOAc/hexane)

Sources & evidence

ORD record
ord-62efbca5ee5949cd9fa9fa60f67e1589
Source dataset
uspto-grants-2007_06
Patent number
US07232826B2

Reaction notes

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