Ammonium Hydroxide → 2-Amino-4-methylbenzonitrile

HRID 471589

反応式

HRID 471589 の反応式
Br[C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([Cu])#[N:12].[NH4+].[OH-]>CN1C(=O)CCC1>[NH2:12][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 8208022-Bromo-4-methylbenzonitrileHCID 178418546HCID 178418546、化合物

生成物 1

HCID 28012762-Amino-4-methylbenzonitrile収率 88%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
0 °C

実験手順

A solution of 2-bromo-4-methylbenzonitrile (2.0 g, 10.7 mmol) and CuCN (1.92 g, 21.4 mmol) in NMP (10 mL) was reacted in a microwave for 20 min at 200° C. Upon completion the reaction was cooled to 0° C., and 15% aqueous NH4OH (215 mL) was slowly added. The mixture was stirred at rt for 30 min, then extracted with CH2Cl2. The organic layer was washed with H2O, brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (3:1 Hexane:EtOAc) to provide 2-amino-4-methylbenzonitrile (1.24 g, 88%). 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 3H), 5.70 (m, 1H), 5.84 (m, 1H), 6.41 (d, J=8.0 Hz, 1H).

後処理

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (3:1 Hexane:EtOAc)

出典と根拠

ORDレコード
ord-2e355610288649758aedb4884ecb2884
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

関連ノート

読み込み中…