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Hydrazine hydrate (1:1) → (5,7-Difluoroquinolin-6-yl)methanamine

HRID 1959758
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HRID 1959758 반응식
[F:1][C:2]1[C:11]([CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)=[C:10]([F:24])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.O.NN>CO>[F:1][C:2]1[C:11]([CH2:12][NH2:13])=[C:10]([F:24])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2
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참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 698103402-(5,7-Difluoroquinolin-6-ylmethyl)isoindoline-1,3-dione

생성물 1

HCID 66994774(5,7-Difluoroquinolin-6-yl)methanamine수율 88.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2-(5,7-difluoroquinolin-6-ylmethyl)isoindoline-1,3-dione (5.10 g, 15.73 mmol) in CH3OH (150 mL) was added hydrazine monohydrate (0.50 g, 15.73 mmol). The solution was heated at reflux for 3 h. After cooling, the mixture was filtered through celite. The filtrate was concentrated in vacuo. EtOAc was added to dilute the residue, filtered and concentrated in vacuo to afford (5,7-difluoroquinolin-6-yl)methanamine (2.70 g, 88%). 1H-NMR (400 MHz, CDCl3) δ ppm 8.93 (d, 1H), 8.38 (d, 1H), 7.59 (d, 1H), 7.43 (m, 1H), 4.12 (s, 2H). LCMS (method B): [MH]+=195.0, tR=0.17 min.

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후처리

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionEtOAc was added
  7. additionto dilute the residue
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-99ddfd0ec0f44ce89739c4d09fae7067
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410264B2

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