Hydroxyamine hydrochloride → HCID 178450317, compound

HRID 978989Notes

Reaction equation

HRID 978989 reaction equation
[C:1]([C:6]1[C:7](=[O:24])[CH2:8][CH:9]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[C:15]([CH:21]=O)[C:14]=2[CH3:23])[CH2:10][C:11]=1[OH:12])(=[O:5])[CH2:2][CH2:3][CH3:4].Cl.[NH2:26]O>C(O)=O>[C:1]([C:6]1[C:7](=[O:24])[CH2:8][CH:9]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[C:15]([C:21]#[N:26])[C:14]=2[CH3:23])[CH2:10][C:11]=1[OH:12])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178450318HCID 178450318, compound

Product 1

HCID 178450317HCID 178450317, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-butyryl-3-hydroxy-5-(3-formyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (1.50 g) and hydroxylamine hydrochloride (0.35 g) in 98% formic acid (7 ml) was refluxed for an hour and then allowed to cool. The mixture was diluted with ice water and the precipitate collected. Purification by column chromatography over silica gel (eluant dichloromethane) gave 2-butyryl-3-hydroxy-5-(3-cyano-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.67 g; 44%) as a pale yellow oil. Proton nuclear magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.00 (3H, t); 1.68 (2H, m); 2.45 (6H, s); 2.60 (3H, s); 2.65-4.20 (7H, m); 7.42 (1H, s); 18.35 (1H, s).

Workup

  1. temperatureto cool
  2. customthe precipitate collected
  3. customPurification by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-fadf057cfa884644991c38f73e5b8e1d
Source dataset
uspto-grants-1987_05
Patent number
US04666510

Reaction notes

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