Triethylamine → HCID 53973932, compound

HRID 342941Notes

Reaction equation

HRID 342941 reaction equation
C([N:3](CC)CC)C.C(O[CH:11]=[C:12]([C:24](=[O:26])[CH3:25])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])=[O:14])C.Cl.NO>C(#N)C>[N+:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]([C:12]1[CH:11]=[N:3][O:26][C:24]=1[CH3:25])=[O:14])([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 54565302HCID 54565302, compound

Product 1

HCID 53973932HCID 53973932, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (1.9 g) was added to a mixture of 2-ethoxymethylene-1-(2-nitrophenyl)-butan-1,3-dione (4.9 g) and hydroxylamine hydrochloride (1.3 g) in acetonitrile (100 ml) with stirring. The mixture was stirred for 2 hours and left to stand overnight. The mixture was evaporated almost to dryness and water (100 ml) was added. The mixture was extracted with ethyl acetate (2×75 ml), dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 4(2-nitrobenzoyl)-5-methylisoxazole (compound 2, 2.4 g) as a brown solid, mp 104.5°-105.5° C.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. waitleft
  3. customThe mixture was evaporated almost to dryness and water (100 ml)
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate (2×75 ml)
  6. dry with materialdried (anhydrous magnesium sulphate)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-3658e63962ba4c72b0b2d530e018799c
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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