Stannous chloride dihydrate → 2-(3-Aminophenyl)-2-methylpropanenitrile

HRID 1918055Notes

Reaction equation

HRID 1918055 reaction equation
O.O.[Sn](Cl)Cl.[CH3:6][C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=1)([CH3:10])[C:8]#[N:9]>CCO>[NH2:17][C:13]1[CH:12]=[C:11]([C:7]([CH3:10])([CH3:6])[C:8]#[N:9])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 155413242-Methyl-2-(3-nitrophenyl)propanenitrile

Product 1

HCID 569657872-(3-Aminophenyl)-2-methylpropanenitrileYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of tin (II) chloride bis hydrate (3.3 g, 13.1 mmol) in EtOH (25 mL) was added 2-methyl-2-(3-nitrophenyl)propanenitrile (800 mg, 4.2 mmol). The reaction mixture was stirred at 90° C. for 1 h. After cooling down to rt, the solvent was removed under reduced pressure and the residue taken in DCM, washed with water and a saturated solution of sodium hydrogen carbonate until pH=8. After combining, the organics were dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (hexane/ethyl acetate 15%) to afford 2-(3-aminophenyl)-2-methylpropanenitrile (490 mg, 73%) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ 1.69 (s, 6H), 3.75 (brs, 2H), 6.64 (d, J=9 Hz, 1H), 6.80-6.83 (m, 2H), 7.15-7.19 (m, 1H); LC-MS (ESI) m/z 161 (M+H)+.

Workup

  1. temperatureAfter cooling down to rt
  2. customthe solvent was removed under reduced pressure
  3. washwashed with water
  4. dry with materialthe organics were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate 15%)

Sources & evidence

ORD record
ord-31e2c0dd3d09484bbefb083b69437528
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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