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Formic Acid → 4-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yloxy)benzaldehyde

HRID 2423563
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HRID 2423563 반응식
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([O:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#N)=[CH:13][CH:12]=1)[CH2:6]2.C(O)=[O:20]>[Ni]>[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:20])=[CH:13][CH:12]=1)[CH2:6]2
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참가 물질

4

반응물 2

HCID 284Formic AcidHCID 113569274-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yloxy)benzonitrile

생성물 1

HCID 579340574-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yloxy)benzaldehyde

시약·촉매·용매 1

HCID 935Nickel촉매

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온도
100 °C

실험 절차

The title compound was synthesized by referring to Chem. Pharm. Bull., 1991, 39, 1440. To a solution of 4-(8-methyl-8-azabicyclo[3.2.1]oct-3-yloxy)benzonitrile (300 mg) in formic acid (5 ml) was added Raney nickel (50% suspension in water) (1 ml), and the solution was stirred for 2 hours at 100° C. After filtration through celite pad and several wash with tetrahydrofuran and methanol, the solvent was evaporated in vacuo, and the resulting residue was neutralized by adding a saturated aqueous solution of sodium bicarbonate. After extraction with chloroform and washing with brine, the solution was dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo to provide the title compound (266 mg).

후처리

  1. customThe title compound was synthesized
  2. filtrationAfter filtration through celite pad
  3. washseveral wash with tetrahydrofuran and methanol
  4. customthe solvent was evaporated in vacuo
  5. additionby adding a saturated aqueous solution of sodium bicarbonate
  6. extractionAfter extraction with chloroform
  7. washwashing with brine
  8. dry with materialthe solution was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-040a402d0a88439f884c1f874692cb52
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960412B2

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