N-[4-(hydroxymethyl)-3-methylphenyl]acetamide → N-(4-Formyl-3-methylphenyl)acetamide

HRID 644730노트

반응식

HRID 644730 반응식
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[CH3:13]>C(#N)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[CH3:13])=[O:1]

참가 물질

4

반응물 1

HCID 54053024N-[4-(hydroxymethyl)-3-methylphenyl]acetamide

생성물 1

HCID 12931765N-(4-Formyl-3-methylphenyl)acetamide수율 92%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

N-[4-(Hydroxymethyl)-3-methylphenyl]acetamide (D77) (0.36 g, 2 mmol) and manganese dioxide (0.875 g, 10 mmol) were combined in acetonitrile (16 mL) and heated to 120° C. in the microwave for 7 minutes. The MnO2 was filtered off and the reaction mixture was concentrated to give the crude product which was purified by column chromatography. Elution with 0-100% ethyl acetate/petroleum ether yielded the title compound as a cream solid (0.326 g). δH (CDCl3, 400 MHz) 10.17 (1H, s), 7.77 (1H, d), 7.51 (1H, d), 7.45 (1H, s), 7.36 (1H, br.s), 2.66 (3H, s), 2.22 (3H, s). MS (ES): MH+ 178.2.

후처리

  1. filtrationThe MnO2 was filtered off
  2. concentrationthe reaction mixture was concentrated
  3. customto give the crude product which
  4. customwas purified by column chromatography
  5. washElution with 0-100% ethyl acetate/petroleum ether

출처 및 근거

ORD 기록
ord-f747859b9e824acf989c8331146d1106
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700599B2

반응 노트

불러오는 중…