Ammonia → 2-Amino-3-methylbenzonitrile

HRID 711620ノート

反応式

HRID 711620 の反応式
Br[C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[C:10]([Cu])#[N:11].N>CN1C(=O)CCC1>[NH2:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[C:10]#[N:11]

参加物

5

反応物 3

HCID 222AmmoniaHCID 27562502-Bromo-6-methylanilineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 108554942-Amino-3-methylbenzonitrile

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To a solution of 2-bromo-6-methylaniline (126 μL, 1 mmol) in dry NMP (3 mL) was added CuCN (197 mg, 2.2 mmol). The mixture was irradiated in a microwave at 220° C. for 40 minutes, cooled to room temperature and poured into a mixture of ammonia (50% w/v, 10 mL) and ice. The mixture was stirred for 30 min and the product was extracted with dichloromethane (3×20 mL). The organic layers were combined, washed with water and brine, dried over MgSO4 and concentrated. The crude material was purified on silica gel (50% EtOAc/hexanes) to yield a brown oil that crystallized on standing (128 mg, 96%). 1H NMR (400 MHz, DMSO-d6) δ 2.08 (s, 3H), 5.68 (bs, 2H), 6.51-6.55 (t, 1H), 7.17-7.19 (d, 1H), 7.22-7.24 (dd, 1H). MS 133 (MH+).

後処理

  1. customThe mixture was irradiated in a microwave at 220° C. for 40 minutes
  2. extractionthe product was extracted with dichloromethane (3×20 mL)
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified on silica gel (50% EtOAc/hexanes)
  7. customto yield a brown oil that
  8. customcrystallized

出典と根拠

ORDレコード
ord-0870a63ae64a4768af555896cbedd315
出典データセット
uspto-grants-2015_11
特許番号
US09181276B2

反応ノート

読み込み中…