Hydrazine hydrate (1:1) → 1-(7-Amino-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

HRID 729234노트

반응식

HRID 729234 반응식
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-])=O)=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].O.NN>CO>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([NH2:14])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 64254731-(7-Nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

생성물 1

HCID 128113521-(7-Amino-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one수율 86.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 13 (5.1 g, 23 mmol), activated carbon (4.2 g), ferric chloride hexahydrate (2.1 g, 7.6 mmol) and methanol (140 ml) is stirred under refluxing for 20 minutes. To the boiling mixture is added hydrazine hydrate (8.5 g, 265 mmol) dropwise, and the mixture is refluxed for an additional 4 h, cooled and filtered and the residue washed with methanol. The filtrate is concentrated in vacuo and the residue recrystallized from EtOAc to give compound 14 (3.8 g, 85% yield). 1H NMR [300 MHz, (CD3)2SO], a 3:2 mixture of amide conformers doubling most signals, δ 6.80 (1H, d, H-5), 6.40 (1H, d, H-6), 6.33 (1H, s, H-7), 4.89 (2H, br s, NH2), 4.46 (0.8H, s, ArCH2N), 4.41 (1.2H, s, ArCH2N), 3.57 (2H, t, ArCH2CH2N), 2.66 (1.2H, t, ArCH2CH2N), 2.55 (0.8H, t, ArCH2CH2N), 2.06 (1.2H, s, COCH3), 2.05 (1.8H, s COCH3).

후처리

  1. temperatureunder refluxing for 20 minutes
  2. temperaturethe mixture is refluxed for an additional 4 h
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe residue washed with methanol
  6. concentrationThe filtrate is concentrated in vacuo
  7. customthe residue recrystallized from EtOAc

출처 및 근거

ORD 기록
ord-10052024dbfd4794a38efb33a52ab770
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582616B2

반응 노트

불러오는 중…