Hydroxyamine hydrochloride → HCID 178450317, compound

HRID 35774Notes

Reaction equation

HRID 35774 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): 100 (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-ebded0c30626469f91ef6c40ba7c24a1
Source dataset
uspto-grants-1988_08
Patent number
US04767879

Reaction notes

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