Hydrogen Bromide → Benzylhydroxylamine

HRID 328358Notes

Reaction equation

HRID 328358 reaction equation
CO[C:3]1[CH:11]=[CH:10][C:6]([CH2:7][NH:8][OH:9])=[CH:5][CH:4]=1.Br.C1(O)C=CC=CC=1>C(O)(=O)C>[CH2:7]([NH:8][OH:9])[C:6]1[CH:10]=[CH:11][CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 10909770N-(4-Methoxybenzyl)hydroxylamine

Product 1

HCID 2794173BenzylhydroxylamineYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.28 g (4 mmoles) of N-benzyl-N-mesyl-O-(p-methoxybenzylhydroxylamine prepared as described in Example 1 was treated with 15 ml of a 38% hydrogen bromide solution in acetic acid at room temperature for 20 hours in the presence of 1.5 g of phenol, and the mixture was then concentrated under a reduced pressure. 30 ml of diethyl ether and 10 ml of water and were then added to the resulting residue, and the aqueous layer was separated, concentrated under a reduced pressure to a small volume, adjusted to a pH of 8 with sodium carbonate and allowed to stand for 5 hours in a refrigerator. The crystals precipitated were collected by filtration to obtain 0.15 g (33% yield) of N-benzylhydroxylamine having a melting point of 56°-57° C. (The melting point reported in the literature is 57° C).

Workup

  1. concentrationthe mixture was then concentrated under a reduced pressure
  2. addition30 ml of diethyl ether and 10 ml of water and were then added to the resulting residue
  3. customthe aqueous layer was separated
  4. concentrationconcentrated under a reduced pressure to a small volume
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-75343f05dade4f5caf1b2f035b45728e
Source dataset
uspto-grants-1977_04
Patent number
US04017512

Reaction notes

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