1-Cyclopentyloxy-2-methoxy-5-nitrobenzene → 3-(Cyclopentyloxy)-4-methoxyaniline

HRID 47600

반응식

HRID 47600 반응식
[CH:1]1([O:6][C:7]2[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=2[O:16][CH3:17])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[CH:1]1([O:6][C:7]2[CH:12]=[C:11]([CH:10]=[CH:9][C:8]=2[O:16][CH3:17])[NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 1

HCID 113907411-Cyclopentyloxy-2-methoxy-5-nitrobenzene

생성물 1

HCID 27793343-(Cyclopentyloxy)-4-methoxyaniline수율 95.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a suspension of 10% Pd on activated carbon (25 g) in ethanol (4L), under N2 protection, was added 1-cyclopentyloxy-2-methoxy-5-nitrobenzene (250 g, 1.054 mol). The reaction mixture was degassed under vacuum three times. The reaction mixture was stirred vigorously while hydrogen gas was allowed to flow over the reaction mixture. After 4 h the reaction was complete by TLC (5:1 hex:EA). The reaction mixture was filtered through a pad of celite and the celite was rinsed with additional ethanol. The solvent was removed in-vacuo to obtain 208.38 g (95% yield) of 3-cyclopentyloxy-4-methoxyaniline as a red liquid. 1H NMR (CDCl3) δ 6.85 (d. J=8.4 Hz, 1H), 6.29 (s, 1H), 6.19 (dd, J=2.8, 8.4, 1H), 4.69 (p, J=4.4 Hz, 1H), 3.75 (s, 3H), 3.44 (bs, 2H),1.90-1.81 (m, 6H), 1.61-1.55 (m, 2H).

후처리

  1. customThe reaction mixture was degassed under vacuum three times
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washthe celite was rinsed with additional ethanol
  4. customThe solvent was removed in-vacuo

출처 및 근거

ORD 기록
ord-a78c2e88d66048de9707ae4a9542d381
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699890B2

연결된 노트

불러오는 중…