Hydrochloric Acid → 3-(4-Nitrophenyl)isoxazole-5-carboxylic acid

HRID 75819

Reaction equation

HRID 75819 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([C:15]([O:17]CC)=[O:16])[O:12][N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Cl>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[O:12][N:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9493753-(4-Nitro-phenyl)-isoxazole-5-carboxylic acid ethyl ester

Product 1

HCID 431501293-(4-Nitrophenyl)isoxazole-5-carboxylic acidYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(4-nitrophenyl)isoxazole-5-carboxylate (11 g) was dissolved in THF (220 ml). 1 Molar aqueous NaOH (210 ml) was added and stirred at RT for 15-20 minutes. The reaction mass was acidified with 1 molar HCl. The reaction mixture was extracted with ethyl acetate, organic layer washed with brine, dried over Na2SO4 and concentrated under reduced pressure to get off white solid. Solid was crystallized from acetone/Pet ether to yield 8 g (81%) white solid. MS (ES+): m/z 235 (M+1); 1H NMR (DMSO-d6, 300 MHz) δ: 8.39 (d, 2H), 8.27 (d, 2H), 7.97 (s, 1H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate, organic layer
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get off white solid
  6. customSolid was crystallized from acetone/Pet ether

Sources & evidence

ORD record
ord-62dbc791cc774af99fdcc970673b6275
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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