Ammonia → 2-Amino-4-(4-chloro-phenyl)-butyronitril

HRID 1159186Notes

Reaction equation

HRID 1159186 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=O)=[CH:4][CH:3]=1.C[Si]([C:16]#[N:17])(C)C.[NH3:18].CO>[I-].[Zn+2].[I-]>[NH2:18][CH:10]([CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:16]#[N:17]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 82115Trimethylsilyl cyanideHCID 115356223-(4-Chlorophenyl)propanal

Product 1

HCID 686441462-Amino-4-(4-chloro-phenyl)-butyronitrilYield 50%

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

To 3-(4-chlorophenyl)-propionaldehyde (0.74 g, 4.39 mmol) was added zinc iodide (0.07 g, 0.22 mmol) and trimethylsilyl cyanide (0.522 g, 5.27 mmol) with caution (exothermic reaction). After stirring the mixture at room temperature for 20 min a solution of ammonia in methanol (7N, 4.4 ml, 31 mmol) was added and stirring was continued overnight. The solvent was evaporated and the residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent:heptane/ethyl acetate=2:1) to yield a light yellow liquid (0.43 g, 50%); MS (ISP): 195.3 ((M+H)+).

Workup

  1. customwith caution (exothermic reaction)
  2. additionwas added
  3. customThe solvent was evaporated
  4. customthe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent:heptane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b79152eac4264d188a4e763a817900e9
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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