Ammonia → HCID 3739483, compound

HRID 1889695Notes

Reaction equation

HRID 1889695 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)/[CH:10]=[N:11]/O)=[CH:4][CH:3]=1.N>C(O)C.[Ni]>[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:10][NH2:11])[CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58531385HCID 58531385, compound

Product 1

HCID 3739483HCID 3739483, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a mixture of (E)-3-(4-fluorophenoxy)benzaldehyde oxime (3.0 g, 12.9 mmol, 1.0 eq) in ethanol, was added Raney nickel (300 mg, 10% wt/wt) followed by aqueous ammonia (10% in volume). The reaction mixture was stirred at ambient temperature under hydrogen pressure for 4 h, before being filtered. The filtrate was concentrated under high vacuum to obtain the desired compound (1.8 g, 64%). 1H NMR (400 MHz, DMSO-d6) δ 7.30-7.17 (m, 3H), 7.07-6.80 (m, 4H), 6.79-6.76 (t, 1H), 3.67 (s, 1H). MS (ESI): 218.2 (M+H)+.

Workup

  1. filtrationbefore being filtered
  2. concentrationThe filtrate was concentrated under high vacuum

Sources & evidence

ORD record
ord-73cf7bbff06041d18439cbfb665a0851
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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