Hydroxylamine → 3-Butyn-2-amine, 4-[3-(4-fluorophenoxy)phenyl]-N-hydroxy-

HRID 861686Notes

Reaction equation

HRID 861686 reaction equation
Br[CH:2]([C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:7]=1)[CH3:3].[NH2:20][OH:21]>CN1CCCC1=O.O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:8]2[CH:7]=[C:6]([C:5]#[C:4][CH:2]([NH:20][OH:21])[CH3:3])[CH:11]=[CH:10][CH:9]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 108601322-Bromo-4-[3-(4-fluorophenoxy)phenyl]-3-butyne

Product 1

HCID 107545733-Butyn-2-amine, 4-[3-(4-fluorophenoxy)phenyl]-N-hydroxy-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The 2-bromo-4-[3-(4-fluorophenoxy)phenyl]-3-butyne prepared in step 2 was taken up in N-methyl-2-pyrollidinone (27 kg) and 50% aqueous hydroxylamine (21 kg) was added. The reaction mixture was agitated for 2.5 hours at ambient temperature and then was diluted with distilled water (18 kg). The layers were separated and the organic phase was concentrated in vacuo to give N-[4-(3-(4-fluorophenoxy)phenyl)-3-butyn-2-yl]hydroxylamine.

Workup

  1. customThe layers were separated
  2. concentrationthe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-97e99734196f448398e6b0f34db326ac
Source dataset
uspto-grants-1998_02
Patent number
US05714633

Reaction notes

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