1-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole → 3-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline

HRID 475715

반응식

HRID 475715 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[N:15][C:14]([CH3:17])=[N:13]1>[Pd].CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[N:15][C:14]([CH3:17])=[N:13]1)[NH2:9]

참가 물질

4

반응물 1

HCID 595777881-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

생성물 1

HCID 595778183-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline수율 94.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

10% Palladium on carbon (1.2 g) was added under an atmosphere of nitrogen to a chilled (ice-water bath) solution of 1-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (3.7 g, 12.7 mmol) dissolved in methanol (250 mL). The flask was repeated evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to warm to rt and left to stir for 18 h under the hydrogen atmosphere. Purged with nitrogen gas. Filtered the crude reaction mixture through a short diatomaceous earth (Celite®) plug. Rinsed reaction vessel and plug with methanol. Concentrated filtrate in vacuo. Dried residue on high vacuum overnight to afford 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (2.44 g, 94% yield) as a reddish solid. LC-MS (M+H)+ 205.2. 1H NMR (500 MHz, CDCl3) δ ppm 8.35 (s, 1H) 7.36 (d, J=8.55 Hz, 1H) 6.29-6.34 (m, 2H) 3.80 (s, 3H) 2.46 (s, 3H).

후처리

  1. customThe flask was repeated evacuated
  2. customflushed with hydrogen gas (double balloon)
  3. waitleft
  4. customPurged with nitrogen gas
  5. filtrationFiltered the crude
  6. customreaction mixture through a short diatomaceous earth (Celite®) plug
  7. washRinsed
  8. customreaction vessel and plug with methanol

출처 및 근거

ORD 기록
ord-a23154dc9257412eae402184617fad35
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637525B2

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