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

HRID 75819

반응식

HRID 75819 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-62dbc791cc774af99fdcc970673b6275
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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