2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl- → HCID 178428731, compound

HRID 1419110Notes

Reaction equation

HRID 1419110 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][C:5]1[C:6](=[O:14])[C:7]([CH3:13])=[C:8]([CH3:12])[C:9](=O)[CH:10]=1>O.CO>[CH3:13][C:7]1[C:6](=[O:14])[C:5]([CH3:4])=[CH:10][C:9](=[N:2][OH:3])[C:8]=1[CH3:12]

Participants

5

Reactant 2

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178428731HCID 178428731, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 7.04 g of hydroxylamine hydrochloride in 30 ml of water was added at room temperature to a solution of 16.9 g of trimethylbenzoquinone (prepared as described in Preparation 10) in 150 ml of methanol, and the resulting mixture was stirred for 2 hours, after which it was allowed to stand for 2 days. At the end of this time, the reaction mixture was diluted with 1000 ml of water. The precipitate which separated out was collected by filtration and recrystallized from a mixture of ethyl acetate and hexane, to give 11.2 g of the title compound, melting at 188°-190° C.

Workup

  1. waitto stand for 2 days
  2. customThe precipitate which separated out
  3. filtrationwas collected by filtration
  4. customrecrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-935864ed732a47989361e52e79d7a6a6
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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