Sodium Hydroxide → 2-Amino-5-methylbenzonitrile

HRID 711618ノート

反応式

HRID 711618 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[C:7]#[N:8].Cl[Sn]Cl.[OH-].[Na+]>Cl.CCO>[NH2:10][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:9][C:6]=1[C:7]#[N:8]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 5607435-Methyl-2-nitrobenzonitrile

生成物 1

HCID 2427782-Amino-5-methylbenzonitrile収率 99.7%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
25 °C

実験手順

5-Methyl-2-nitrobenzonitrile (1.92 g, 11.84 mmol) was added in portions to a stirred solution of SnCl2 (11.22 g, 59.2 mmol) in conc. HCl (12 mL) and EtOH (12 mL). The reaction temperature was maintained at 20-30° C. using an ice bath. The reaction mixture was then stirred at room temperature for 1 h and poured into an ice cold aqueous solution of NaOH (6N, app. 30 mL) to neutralize to pH7. The product was extracted into EtOAc, washed with brine, dried over MgSO4 and concentrated to provide the title product (1.56 g, 99%) as a yellow-brown solid. 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 3H), 5.79 (bs, 2H), 6.68-6.71 (d, 1H), 7.10-7.13 (dd, 1H), 7.15 (s, 1H). 13C NMR (DMSO-d6) δ 20.13, 93.99, 116.12, 118.94, 125.38, 132.32, 135.76, 150.21. MS 133 (MH+).

後処理

  1. extractionThe product was extracted into EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-ccdd148f97f04b6ca557271d87c266d8
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…