Acetic Acid → N2-(1-(quinolin-2-yl)azetidin-3-yl)pyridine-2,3-diamine

HRID 707344노트

반응식

HRID 707344 반응식
[N+:1]([C:4]1[C:5]([NH:10][CH:11]2[CH2:14][N:13]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)[CH2:12]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.C(O)(=O)C>C(O)C.O.[Fe]>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[N:13]1[CH2:14][CH:11]([NH:10][C:5]2[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:12]1

참가 물질

6

반응물 2

HCID 176Acetic AcidHCID 866942023-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine

생성물 1

HCID 86694203N2-(1-(quinolin-2-yl)azetidin-3-yl)pyridine-2,3-diamine수율 81.2%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
95 °C

실험 절차

To a solution of 3-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine (1.05 g, 3.20 mmol) in ethanol (30 mL) and water (10 mL) was added iron (448 mg, 8.0 mmol) and acetic acid (240 mg, 4.0 mmol) slowly dropwise. The mixture was heated at 95° C. until TLC analysis confirmed the absence of starting materials. The reaction mixture was filtered through a plug of CELITE™ washing with methanol. The black filtrate was concentrated in vacuo, treated with brine (40 mL) and extracted with dichloromethane (3×60 mL). The combined organic extracts were washed with water (30 mL) and brine (30 mL) and then dried over sodium sulfate. The filtrate was evaporated in vacuo to give N2-(1-(quinolin-2-yl)azetidin-3-yl)pyridine-2,3-diamine (0.744 g, 2.6 mmol, yield 80%).

후처리

  1. filtrationThe reaction mixture was filtered through a plug of CELITE™
  2. washwashing with methanol
  3. concentrationThe black filtrate was concentrated in vacuo
  4. additiontreated with brine (40 mL)
  5. extractionextracted with dichloromethane (3×60 mL)
  6. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  7. dry with materialdried over sodium sulfate
  8. customThe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-b28e388cbf574c348ff6dcbf723cd7b0
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

반응 노트

불러오는 중…