Nitromethane → Nitroethane

HRID 429274Notes

Reaction equation

FC(F)(F)[C:3]1C=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(O[CH2:17][CH3:18])(=[O:15])C#C.[N+:19](C)([O-:21])=[O:20]>>[N+:19]([CH2:17][CH3:18])([O-:21])=[O:20].[CH3:7][C:6]1[CH:5]=[C:4]([CH3:3])[O:15][N:8]=1

Participants

Reactant 3

HCID 6375Nitromethane

HCID 99644-(Trifluoromethyl)aniline

HCID 12182Ethyl propiolate

Product 2

HCID 6587Nitroethane

HCID 93123,5-Dimethylisoxazole

Procedure

By substituting 5-amino-1,3-benzodioxole for 4-(trifluoromethyl)aniline in a, and then substituting the appropriate substituted propiolic ester for ethyl propiolate and/or the appropriate stubstituted nitromethane for nitroethane in a, the identical process gives 4-(1,3-benzodioxol-5-aminocarbonyl)-3-methylisoxazole, 4-(1,3-benzodioxol-5-aminocarbonyl)-3-cyclopropylisoxazole, 4-(1,3-benzodioxol-5-aminocarbonyl])-3,5-dimethylisoxazole, 4-(1,3-benzodioxol-5-aminocarbonyl)-3-cyclopropyl-5-methylisoxazole, and 4-(1,3-benzodioxol-5-aminocarbonyl)-5-(2-chlorophenyl)-3-methylisoxazole, and 4-(1,3-benzodioxol-5-aminocarbonyl)-5-(2-chlorophenyl)-3-cyclopropylisoxazole.

Sources & evidence

ORD record: ord-3222056e036a4ee49eae2cfb5032a1b6
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06316479B1

Reaction notes

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