Pyridine → N-Acetyl-3-(3,5-di-t-butyl-4-hydroxyanilino)benzoic Acid

HRID 2254877

반응식

HRID 2254877 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])([CH3:4])([CH3:3])[CH3:2].[C:26](OC(=O)C)(=[O:28])[CH3:27].N1C=CC=CC=1>N1C=CC=CC=1.O>[C:26]([N:8]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])[C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:20]([OH:21])=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=1)(=[O:28])[CH3:27]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 7918Acetic Anhydride2회HCID 601943-(3,5-DI-T-Butyl-4-hydroxyanilino)benzoic acid

생성물 1

HCID 15340644N-Acetyl-3-(3,5-di-t-butyl-4-hydroxyanilino)benzoic Acid

시약·촉매·용매 2

HCID 1049Pyridine촉매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of 5.6 g of 3-(3,5-di-t-butyl-4-hydroxyanilino)benzoic acid (from Example 13) and 15 ml of acetic anhydride was heated under a nitrogen atmosphere at 70°-120° C. for about 90 minutes. The mixture was cooled to 80° C., 5 drops of pyridine were added and the reaction was reheated to 120° C. for 10 minutes. An additional 0.25 ml of pyridine was added at about 80° C., followed by the gradual addition of 10 ml of water to hydrolyze the excess acetic anhydride and the mixed anhydride of the product. Heating was continued until a precipitate formed. The reaction mixture was allowed to cool to room temperature, and the precipitate was then collected, rinsed with a cold mixture of methanol and water, and dried to give 4.3 g of off-white solid m.p. 204°-205.5° C. This material was recrystallized first from a mixture of 30 ml of ethanol and 5 ml of water, and then from a mixture of 30 ml of isopropanol and 5 ml of hexane to give 3.3 g of white solid N-acetyl-3-(3,5-di-t-butyl-4-hydroxyanilino)benzoic acid m.p. 214.5°-215.5° C. Analysis: Calculated for: C23H29NO4. 1/2(CH3)2CHOH: %C, 71.2; %H, 8.0; %N 3.4. Found: %C, 71.4; %H, 8.1; %N, 3.2.

후처리

  1. temperaturewas heated under a nitrogen atmosphere at 70°-120° C. for about 90 minutes
  2. temperatureHeating
  3. customformed
  4. temperatureto cool to room temperature
  5. customthe precipitate was then collected
  6. washrinsed with a cold mixture of methanol and water
  7. customdried

출처 및 근거

ORD 기록
ord-ea5f5a9d7caa4c1a875d7e863e4a18a2
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05237070

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