Sodium Hydroxide → 2-Amino-5-methylbenzonitrile

HRID 2076964

반응식

HRID 2076964 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 2427782-Amino-5-methylbenzonitrile수율 99.7%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

반응 조건

온도
25 °C

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-d8f05fcea28f48109704229eab3430f4
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928111B2

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