Hydroxyamine hydrochloride → 3-Fluoro-4-nitro-benzaldehyde oxime

HRID 75793Notes

Reaction equation

HRID 75793 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=O.Cl.[NH2:14][OH:15]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[N:14][OH:15]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 38081203-Fluoro-4-nitrobenzaldehyde

Product 1

HCID 762213223-Fluoro-4-nitro-benzaldehyde oximeYield 77.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
62.5 °C

Procedure

A mixture of 3-fluoro-4-nitro-benzaldehyde (9.5; 56.21 mmol) and hydroxylamine hydrochloride (4.29 g; 61.83 mmol) in ethanol (50 mL) was heated at 60-65° C. for 2 hours. The solvent was distilled off. The residue was purified by flash chromatography over silica gel with 10-15% ethyl acetate in light petroleum to give 8 g of the title compound (77.4%); IR (KBr): 3091, 3056, 2501, 2431, 1597, 1513, 1488, 1400 cm−1; MS (m/z): 185 (M++1); 1H NMR (CDCl3) δ: 7.62-7.70 (m, 2H), 8.14-8.19 (m, 1H), 8.24 (s, 1H NH), 11.99 (s, 1H, NHOH).

Workup

  1. distillationThe solvent was distilled off
  2. customThe residue was purified by flash chromatography over silica gel with 10-15% ethyl acetate in light petroleum

Sources & evidence

ORD record
ord-0697bcd082d546d199924cb92916bfe5
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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