Hydroxyamine hydrochloride → HCID 58257128, compound

HRID 2093783Notes

Reaction equation

HRID 2093783 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][C:3]=1[C:12](=[O:19])[CH:13]=[C:14]([N:16](C)C)[CH3:15].Cl.NO.CC1C=C([N+]([O-])=O)C(C)=CC=1C1ON=C(C)C=1>C(O)C.CO.[Pd]>[CH3:11][C:5]1[CH:4]=[C:3]([C:12]2[O:19][N:16]=[C:14]([CH3:15])[CH:13]=2)[C:2]([CH3:1])=[CH:7][C:6]=1[NH2:8]

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 67168050HCID 67168050, compoundHCID 67170049HCID 67170049, compound

Product 1

HCID 58257128HCID 58257128, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2,5-dimethyl-4-nitrophenyl)-3-(dimethylamino)but-2-en-1-one (Step 2, 100 mg, 0.38 mmol) and hydroxylamine monohydrochloride (132 mg, 1.9 mmol) in ethanol (3 mL) was heated in a microwave at 100° C. for 15 min. The obtained 5-(2,5-dimethyl-4-nitrophenyl)-3-methylisoxazole was dissolved in methanol (10 mL). To this solution was added Pd/C (10%). The reaction mixture was degassed and purged with H2 for several times and stirred under H2 (1 atm.) overnight. The mixture was filtered and concentrated to afford 2,5-dimethyl-4-(3-methylisoxazol-5-yl)aniline. ESMS m/z 203 (M+H+).

Workup

  1. customThe reaction mixture was degassed
  2. custompurged with H2 for several times
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-add3a68cf8034967aa0a3711d7467ddc
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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