Ammonia → HCID 84050180, compound

HRID 527359Notes

Reaction equation

HRID 527359 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([S:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].N.[H][H]>CO.[Ni]>[F:1][C:2]1[CH:9]=[C:8]([S:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 16753945HCID 16753945, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 84050180HCID 84050180, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-fluoro-4-methylsulfanyl-benzonitrile (8.0 g, 45.5 mmol), Raney-Nickel (20.0 g) and concentrated aqueous ammonia (300 mL) in methanol (3.0 L) is treated with hydrogen (3.4 bar) at room temperature and stirred over night. The mixture is filtered through a pad of silica gel, and the filtrate is concentrated under reduced pressure. Yield: 6.3 g (81% of theory); ESI mass spectrum: [M+H−NH3]+=155; r.t. HPLC: 1.38 min (0-30AB).

Workup

  1. filtrationThe mixture is filtered through a pad of silica gel
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customr.t
  4. custom1.38 min (0-30AB)

Sources & evidence

ORD record
ord-e970261f589d4bee894891512aa95b58
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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