Hydroxylamine → (E)-4-bromo-1-naphthaldehyde oxime

HRID 1958872Notes

Reaction equation

HRID 1958872 reaction equation
[NH2:1][OH:2].[Br:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH:14]=O)=[CH:6][CH:5]=1.BrC1C2C(=CC=CC=2)C(Br)=CC=1>C(O)C>[Br:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH:14]=[N:1][OH:2])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 665211,4-DibromonaphthaleneHCID 46404134-Bromo-1-naphthaldehyde

Product 1

HCID 74016047(E)-4-bromo-1-naphthaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of hydroxylamine (1.25 mL, 50% in water) was added to a stirred solution of 4-bromo-1-naphthalenecarboxaldehyde (3.7 g, 15.7 mmol, prepared from commercially available 1,4-dibromonaphthalene by the method described in European Journal of Organic Chemistry 2006, 10, 2329-2335) in ethanol (30 mL). After stirring at room temperature for 3 h, the reaction mixture was concentrated under reduced pressure to provide the title compound as a pale yellow solid (3.8 g). 1H NMR (Me2S(O)-d6): δ 11.60 (s, 1H), 8.81 (s, 1H), 8.71 (d, 1H), 8.24 (d, 1H), 7.95 (d, 1H), 7.74 (m, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-27d8c234ddaf4d159c26b8b41d90cfa7
Source dataset
uspto-grants-2013_04
Patent number
US08410153B2

Reaction notes

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