Cyclohexene → 2-Amino-6-methoxybenzonitrile

HRID 471609Notes

Reaction equation

HRID 471609 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:4]=1[C:5]#[N:6].C1CCCCC=1>CCO.[Pd]>[NH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[C:4]=1[C:5]#[N:6]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 380482-Methoxy-6-nitrobenzonitrile

Product 1

HCID 127157142-Amino-6-methoxybenzonitrileYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-methoxy-6-nitrobenzonitrile (1.01 g, 5.69 mmol), cyclohexene (2.84 g, 3.51 mL, 34.58 mmol) and 10% Pd/C (0.58 g) in EtOH (25 mL) was refluxed for 1.5 h. The mixture was cooled to room temperature, filtered and evaporated, to afford the title compound 0.83 g (98%). The crude product was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.17 (t, J=8.0 Hz, 1H), 6.31-6.35 (m, 1H), 6.17-6.21 (m, 1H), 5.97 (broad s, 2H), 3.76 (s, 3H).

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-a536d1248c374b86861865c06d22f9a0
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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