Ammonium Acetate → HCID 68292043, compound

HRID 1408937Notes

Reaction equation

HRID 1408937 reaction equation
[CH3:1][C:2]1([C:8]#[N:9])[CH2:6][CH2:5][CH2:4][C:3]1=O.C([O-])(=O)C.[NH4+].C([BH3-])#[N:16].[Na+]>CO>[NH2:16][CH:3]1[CH2:4][CH2:5][CH2:6][C:2]1([CH3:1])[C:8]#[N:9]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 132142491-Methyl-2-oxocyclopentane-1-carbonitrile

Product 1

HCID 68292043HCID 68292043, compoundYield 177.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-methyl-2-oxocyclopentanecarbonitrile (272 mg, 2.209 mmol, from Step 1) and ammonium acetate (917 mg, 11.90 mmol) in methanol (2 mL) was stirred at room temperature for 2 h. Sodium cyanoborohydride (69.4 mg, 1.104 mmol) was added. After 17 h at room temperature, the mixture was concentrated. The residue was dissolved in water and ethyl acetate and stirred vigorously. The ethyl acetate phase was separated, dried (MgSO4), filtered and concentrated to give crude 2-amino-1-methylcyclopentanecarbonitrile (0.2436 g), which was taken to the next reaction without purification.

Workup

  1. waitAfter 17 h at room temperature
  2. concentrationthe mixture was concentrated
  3. dissolutionThe residue was dissolved in water
  4. stirringethyl acetate and stirred vigorously
  5. customThe ethyl acetate phase was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-59c2f0a170244aaca3b11bd2d9b93815
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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