3-Benzyloxy-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid → 5-(benzyloxy)-2-methylpyridin-4(1H)-one

HRID 913040

반응식

HRID 913040 반응식
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[NH:11][C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[NH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

3

반응물 1

HCID 672824263-Benzyloxy-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

생성물 1

HCID 63247195-(benzyloxy)-2-methylpyridin-4(1H)-one수율 77%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

A mixture of 3-benzyloxy-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (5.2 g, 20.0 mmol) in dimethylformamide (12 mL) was heated in an oil bath for 8 h. The temperature of the oil bath was maintained at 120° C. A solid separated upon cooling to RT. The solid 5-benzyloxy-2-methyl-1H-pyridin-4-one was suction filtered and washed with hexane. The isolated solid was dried under high vacuum for 16 h (3.32 g, 77% yield). 1H NMR (400 MHz, MeOH-D4) δ (ppm): 7.45-7.46 (m, overlapping peaks, 2H, Ar—H and CH), 7.29-7.39 (m, overlapping peaks, 4H, Ar—H), 6.34 (s, 1H, CH), 5.07 (s, 2H, OCH2), 2.30 (s, 3H, CH3); MS-ESI (m/z): 216.3 [M+1]+, 215.6 [M]+, 188.3.

후처리

  1. temperaturewas heated in an oil bath for 8 h
  2. customA solid separated
  3. temperatureupon cooling to RT
  4. filtrationfiltered
  5. washwashed with hexane
  6. customThe isolated solid was dried under high vacuum for 16 h (3.32 g, 77% yield)

출처 및 근거

ORD 기록
ord-2e80d71a5ed84d8fbe89bdeb7b434d19
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026261B2

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