Hydroxyamine hydrochloride → 5-[2-Chloro-4-(trifluoromethyl)phenoxy]2-nitrobenzaldehyde oxime

HRID 1249611Notes

Reaction equation

HRID 1249611 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[Cl:9][C:10]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:21]([O-:23])=[O:22])=[C:17]([CH:20]=1)[CH:18]=O>O.C(O)C>[Cl:9][C:10]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:21]([O-:23])=[O:22])=[C:17]([CH:20]=1)[CH:18]=[N:2][OH:3]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 130569775-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzaldehyde

Product 1

HCID 858635775-[2-Chloro-4-(trifluoromethyl)phenoxy]2-nitrobenzaldehyde oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of hydroxylamine hydrochloride (0.33 g., 0.0048 mole) and sodium acetate (0.394 g., 0.0048 mole) in 2-3 ml of water was added a hot solution of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzaldehyde (1.5 g., 0.00434 mole) in ethanol (10-12 ml). The clear yellow solution was heated for 1.5 hours and then the solvent was stripped on a rotary evaporator to give a yellow waxy solid which solidified giving 1.5 g., mp. 111°-115° C. Recrystallization from ethanol/water gave a solid mp. 114°-118° C.

Workup

  1. temperatureThe clear yellow solution was heated for 1.5 hours
  2. customthe solvent was stripped on a rotary evaporator
  3. customto give a yellow waxy solid which
  4. customsolidified giving 1.5 g
  5. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-d9c037e062b548ba8b383e92fe5b4449
Source dataset
uspto-grants-1986_12
Patent number
US04633000

Reaction notes

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