Ammonia → HCID 16790478, compound

HRID 278910Notes

Reaction equation

HRID 278910 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[NH3:11].C[Si]([C:16]#[N:17])(C)C.CCCCCC.CCOC(C)=O>CO>[NH2:11][CH:5]([C:4]1[CH:7]=[CH:8][C:9]([F:10])=[C:2]([F:1])[CH:3]=1)[C:16]#[N:17]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 82115Trimethylsilyl cyanideHCID 5880883,4-DifluorobenzaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 16790478HCID 16790478, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Through a solution of 3,4-difluorobenzaldehyde (25.0 g, 0.18 mol) in MeOH (500 mL) in a round bottom flask was bubbled ammonia gas for two hours at room temperature. The flask was then cooled to 0° C. and trimethylsilyl cyanide (1.3 eq., 0.23 mmol) was then added slowly. The reaction mixture was stirred for 2 hours when TLC analysis indicted that the reaction was complete (Rf=0.35, 3:2 hexane/EtOAc). Solvent was removed in vacuo and the residue was subjected to flash column chromatography on silica gel to obtain 25.0 g (81%) of amino-(3,4-difluorophenyl)-acetonitrile as a yellow syrup.

Workup

  1. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-c5921d2419cb45429b922b05dbf46818
Source dataset
uspto-grants-2002_03
Patent number
US06362182B1

Reaction notes

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