Sodium Hydroxide → 2-(1-Aminoindan-5-yl)-2-methylpropionitrile

HRID 656457Notes

Reaction equation

HRID 656457 reaction equation
[CH3:1][C:2]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=O)[CH2:10][CH2:9]2)([CH3:5])[C:3]#[N:4].C([O-])(=O)C.[NH4+].C([BH3-])#[N:22].[Na+].[OH-].[Na+]>CC(O)C>[NH2:22][CH:11]1[C:12]2[C:8](=[CH:7][C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])=[CH:14][CH:13]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 450989322-Methyl-2-(1-oxo-2,3-dihydro-1H-inden-5-yl)propanenitrile

Product 1

HCID 671892902-(1-Aminoindan-5-yl)-2-methylpropionitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Methyl-2-(1-oxoindan-5-yl)-propionitrile (6.00 g, 30.1 mmol) was added to a mixture of ammonium acetate (69.6 g, 903 mmol) in IPA (600 mL) under nitrogen atmosphere at ambient temperature. After stirring 1 hour, sodium cyanoborohydride (6.62 g, 105 mmol) was added to the mixture and refluxed for 2 hours. The reaction solution was cooled to room temperature, added 3N sodium hydroxide (300 mL), extracted with TBME (2×500 mL) and concentrated the organic extracts to an oil. Dissolved in ethyl acetate (500 mL), extracted with 1N hydrochloric acid (3×300 mL), combined the aqueous layers, added 3N sodium hydroxide (400 mL), extracted with ethyl acetate (2×1 L), dried with brine and anhydrous sodium sulfate, and concentrated. Obtained 2-(1-aminoindan-5-yl)-2-methylpropionitrile (4.26 g, 71%) as a yellow oil. MS (DCI/NH3) m/z: 201.10 [M+H]+. 1H NMR (DMSO-d6) δ: 1.60 (m, 1H), 1.66 (s, 6H), 1.93 (br, 2H), 2.35 (m, 1H), 2.74 (m, 1H), 2.86 (m, 1H), 4.17 (t, 1H), 7.32 (m, 3H).

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with TBME (2×500 mL)
  3. concentrationconcentrated the organic extracts to an oil
  4. dissolutionDissolved in ethyl acetate (500 mL)
  5. extractionextracted with 1N hydrochloric acid (3×300 mL)
  6. additionadded 3N sodium hydroxide (400 mL)
  7. extractionextracted with ethyl acetate (2×1 L)
  8. dry with materialdried with brine and anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e1e9939d6ba24bf1a40e4e12612e3981
Source dataset
uspto-grants-2011_12
Patent number
US08071762B2

Reaction notes

Loading…