Sodium Bicarbonate → 4'-Acetamido-2-hydroxyacetophenone

HRID 32471

반응식

HRID 32471 반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12]Br)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C([O-])=[O:16].[K+].C(=O)(O)[O-].[Na+]>CCO>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][OH:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 2735122Potassium FormateHCID 12364739N-[4-(2-Bromoacetyl)Phenyl]Acetamide

생성물 1

HCID 221825304'-Acetamido-2-hydroxyacetophenone수율 95.2%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
38 °C

실험 절차

To a suspension of 4′-acetamido-2-bromoacetophenone 3 (10.0 g, 39 mmol) in EtOH (800 mL), aqueous potassium formate (35.4 g in 200 mL) was added then followed by sodium bicarbonate (3.68 g). The mixture was stirred at 38° C. (inner temp.) for 22 h. The mixture was evaporated in vacuo until the total volume reached to ca. 300 mL The mixture was diluted with ethyl acetate (1200 mL), washed with water (200 mL), then brine (2×400 mL). Aqueous layers were extracted with ethyl acetate (800 mL then 400 mL). Combined organic layer was dried over anhydrous sodium sulfate and then evaporated in vacuo to give crude 4 as a solid (7.17 g, 95%) which was used to the next step without any purification. MS(ES) m/e 194 [M+H].

후처리

  1. additionwas added
  2. customThe mixture was evaporated in vacuo until the total volume
  3. additionwas diluted with ethyl acetate (1200 mL)
  4. washwashed with water (200 mL)
  5. extractionAqueous layers were extracted with ethyl acetate (800 mL
  6. dry with materialCombined organic layer was dried over anhydrous sodium sulfate
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-e9b276f7adcf4e6382135009aea5fa2d
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427623B2

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