Stannous chloride dihydrate → 4-Amino-2-ethoxybenzonitrile

HRID 1631511

반응식

HRID 1631511 반응식
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[CH3:2].O.O.[Sn](Cl)Cl.C(=O)([O-])O.[Na+]>C(O)C>[NH2:12][C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:11]=1

참가 물질

5

반응물 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 214837232-Ethoxy-4-nitro-benzonitrile

생성물 1

HCID 230680734-Amino-2-ethoxybenzonitrile

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

To a suspension of 2-ethoxy-4-nitro-benzonitrile (0.49 g, 2.54 mmol) in ethanol (50 ml) is added tin (II) chloride dihydrate (2.87 g, 12.7 mmol) and the suspension is stirred at 70° C. for 2 hours and at room temperature overnight. The reaction mixture is poured onto ice-water and the pH of the solution is adjusted to pH 7-8 by addition of sodium hydrogen carbonate solution (5% solution in water). The aqueous emulsion is filtered under vacuum and the product is extracted with ethyl acetate (2×150 ml). The organic portions are combined, washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to yield the titled product as a pale yellow solid which is used in the next step without further purification.

후처리

  1. additionThe reaction mixture is poured onto ice-water
  2. filtrationThe aqueous emulsion is filtered under vacuum
  3. extractionthe product is extracted with ethyl acetate (2×150 ml)
  4. washwashed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6d04053b379949feac93f4102c532022
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791256B2

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