4-(2-methoxy-4-nitrophenyl)-1-methyl-1H-pyrazole → 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline

HRID 1803143ノート

反応式

HRID 1803143 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=1>[Pd].CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[C:12]1[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=1)[NH2:9]

参加物

4

反応物 1

HCID 668604724-(2-methoxy-4-nitrophenyl)-1-methyl-1H-pyrazole

生成物 1

HCID 584144723-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline収率 78%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

Step K (2): 10% Palladium on carbon (1.0 g) was added under an atmosphere of nitrogen to a solution of 4-(2-methoxy-4-nitrophenyl)-1-methyl-1H-pyrazole (10.0 g, 42.9 mmol) in methanol (100 mL). The flask was repeated evacuated and flushed with hydrogen gas. The resulting mixture was allowed to stir at rt for 16 h under. The reaction vessel was purged with nitrogen gas. The crude reaction mixture was filtered 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-(1-methyl-1H-pyrazol-4-yl)aniline (6.8 g, 78% yield). LC-MS (M+H)+ 204.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.84 (s, 1 H) 7.66 (s, 1 H) 7.19 (d, J=8.2 Hz, 1 H) 6.28 (s, 1 H), 6.18 (d, J=8.2 Hz, 1 H) 5.31 (br s, 1 H), 3.88 (s, 3 H), 3.74 (s, 3 H).

後処理

  1. customThe flask was repeated evacuated
  2. customflushed with hydrogen gas
  3. customThe reaction vessel was purged with nitrogen gas
  4. customThe crude reaction mixture
  5. filtrationwas filtered through a short diatomaceous earth (Celite®) plug
  6. washRinsed
  7. customreaction vessel and plug with methanol

出典と根拠

ORDレコード
ord-33e31674192a452190b113790cc5059e
出典データセット
uspto-grants-2013_01
特許番号
US08349880B2

反応ノート

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