Hydroxyamine hydrochloride → HCID 86646188, compound

HRID 1895408Notes

Reaction equation

HRID 1895408 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]=[C:10]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)[C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:24])[CH:3]=1.Cl.[NH2:26][OH:27]>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][C:10]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=3)([C:11]([F:14])([F:13])[F:12])[O:27][N:26]=2)=[C:4]([CH3:24])[CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86646189HCID 86646189, compound

Product 1

HCID 86646188HCID 86646188, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 1-(4-bromo-2-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one (200 mg, 0.45 mmol) in pyridine (3 mL) at room temperature was added hydroxylamine hydrochloride (47 mg, 0.68 mmol). The reaction mixture was heated to reflux for 4 h. The resulting mixture was cooled to room temperature and then concentrated, and the residual oil was purified by chromatography on silica gel using 20:80 ethyl acetate/hexanes as eluent to afford the title product as a pale yellow oil (50 mg, 24% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated
  4. customthe residual oil was purified by chromatography on silica gel using 20:80 ethyl acetate/hexanes as eluent

Sources & evidence

ORD record
ord-c1a672f3dcf4487cb73ed8f91460c5ae
Source dataset
uspto-grants-2013_08
Patent number
US08513431B2

Reaction notes

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