Propionate ion → 3-(2-Nitrophenyl)isoxazolin-5-one

HRID 364832

Reaction equation

HRID 364832 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[C:6]([CH2:8][C:9]([O:11]CC)=[O:10])=O)([O-:3])=[O:2].C([O-])(=O)CC.C([O-])(=O)CCC.Cl.[NH2:30]O.C([O-])(=O)C.[Na+]>C(O)C>[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[C:6]1[CH2:8][C:9](=[O:10])[O:11][N:30]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 104745Propionate ionHCID 104775ButyrateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10561837Ethyl 2-nitro-beta-oxobenzenepropanoate

Product 1

HCID 212718533-(2-Nitrophenyl)isoxazolin-5-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reactions of Equations 15a and 15b above can be run by procedures similar to those described in U.S. Pat. No. 3,781,438 for the preparation of 5-halo-3-phenylisoxazoles. Thus, in reaction 15a, an ethyl 2-(2-nitrobenzoyl)acetate, propionate or butyrate of Formula (XIV) is reacted with hydroxylamine hydrochloride and sodium acetate in ethanol at reflux for 0.5 to 5 hours to form a 3-(2-nitrophenyl)isoxazolin-5-one of Formula (XXVI). In reaction 15b, XXVI is reacted with an equimolar amount of triethylamine and excess phosphorus oxychloride or phosphorus oxybromide in toluene at 25° to 110° C. for 1 to 5 hours to form Xc"'.

Workup

  1. temperatureat reflux for 0.5 to 5 hours

Sources & evidence

ORD record
ord-cb8e304acedb42a3ba4e8998b434a0dc
Source dataset
uspto-grants-1986_08
Patent number
US04606755

Linked notes

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