N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine → N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine

HRID 82631노트

반응식

HRID 82631 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([N+:22]([O-])=O)=[C:20]([CH3:25])[CH:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.C(O)(=O)C.O.[Zn]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([NH2:22])=[C:20]([CH3:25])[CH:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 1

HCID 58577297N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine

생성물 1

HCID 58577506N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine수율 97.4%

시약·촉매·용매 4

HCID 23994Zinc촉매2회HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine (154.5 g) in THF (1300 mL), acetic acid (260 mL) and water (13 mL) was slowly added zinc powder (300 g) over 35 min. After zinc was added, the mixture was stirred at room temperature for 1 h. The reaction mixture was filtered through celite, and insoluble materials were washed with THF (3 L). The filtrate was combined and concentrated. To the residue were added EtOAc (1.2 L) and 2.5 N NaOH (1.2 L) under ice cooling, and then the mixture was stirred at room temperature for 30 min. The mixture was filtered through celite, and insoluble materials were washed with EtOAc (3 L). The organic layer was separated, washed with water (300 mL) and brine (300 mL×2), dried over MgSO4 and concentrated to give a crude N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine (137 g) as black oil. This product was subjected to the next reaction without further purification.

후처리

  1. customover 35 min
  2. filtrationThe reaction mixture was filtered through celite, and insoluble materials
  3. washwere washed with THF (3 L)
  4. concentrationconcentrated
  5. additionTo the residue were added EtOAc (1.2 L) and 2.5 N NaOH (1.2 L) under ice cooling
  6. stirringthe mixture was stirred at room temperature for 30 min
  7. filtrationThe mixture was filtered through celite, and insoluble materials
  8. washwere washed with EtOAc (3 L)
  9. customThe organic layer was separated
  10. washwashed with water (300 mL) and brine (300 mL×2)
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-27003454e7b747e0a75500212e459eec
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846713B2

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