Ethylene Glycol → 6-Nitro-1,2-dihydroisoquinolin-1-one

HRID 708797노트

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HRID 708797 반응식
C[N:2](C)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7](OC)=[O:8].N.C(O)CO>>[N+:15]([C:13]1[CH:14]=[C:5]2[C:6](=[CH:11][CH:12]=1)[C:7](=[O:8])[NH:2][CH:3]=[CH:4]2)([O-:17])=[O:16]

참가 물질

4

반응물 3

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 87664981(E)-Methyl 2-(2-(dimethylamino)vinyl)-4-nitrobenzoate

생성물 1

HCID 707009796-Nitro-1,2-dihydroisoquinolin-1-one수율 85%

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온도
140 °C

실험 절차

To Intermediate 3B (1.54 g, 6.15 mmol) in a microwave tube was added 8.0 N ammonia in ethylene glycol (7.69 mL, 61.5 mmol). The tube was placed in microwave and heated at 140° C. for 30 min. The reaction mixture was triturated with EtOAc, stored at 0° C. over night. The precipitate was collected to give Intermediate 3C (0.995 g, 5.23 mmol, 85% yield) as a brown solid. The filtrate was washed with water. The organic layer was dried over sodium sulfate. After evaporation of solvent, the crude was triturated with EtOAc to give additional product. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.35 (br. s., 1H) 8.63 (d, J=2.20 Hz, 1H) 8.39 (d, J=8.79 Hz, 1H) 8.19 (dd, J=8.79, 2.20 Hz, 1H) 7.36 (d, J=7.03 Hz, 1H) 6.82 (d, 1H); MS (ESI) m/z: 191.1 (M+H)+.

후처리

  1. customThe reaction mixture was triturated with EtOAc
  2. waitstored at 0° C. over night
  3. customThe precipitate was collected

출처 및 근거

ORD 기록
ord-233ece1c319746318debc57332713bfd
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174974B2

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