Tin tetrachloride → 3-Amino-4-chloro-5-ethoxy-benzoic acid methyl ester

HRID 1990862노트

반응식

HRID 1990862 반응식
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([Cl:13])=[C:6]([O:14][CH2:15][CH3:16])[CH:5]=1.[Sn](Cl)(Cl)(Cl)Cl>CO.Cl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:5]=[C:6]([O:14][CH2:15][CH3:16])[C:7]([Cl:13])=[C:8]([NH2:10])[CH:9]=1

참가 물질

5

반응물 2

HCID 24287Tin tetrachlorideHCID 686994194-Chloro-3-ethoxy-5-nitro-benzoic acid methyl ester

생성물 1

HCID 686990463-Amino-4-chloro-5-ethoxy-benzoic acid methyl ester

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

To a solution of 4-chloro-3-ethoxy-5-nitro-benzoic acid methyl ester (1.0 g, 3.85 mmol, 1.0 equiv) in methanol (20 mL) was added dropwise under stirring at 0° C. a solution of tin chloride (2.92 g, 15.41 mmol, 4.0 equiv) in 37% HCl (7.5 mL). After the addition was completed the cooling bath was removed and the reaction mixture stirred at rt for 18 h. The solution was concentrated by evaporation under reduced pressure and the solution extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material purified by recrystallization from dichloromethane yielding 0.88 g (100%) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.28 (t, J=7.0 Hz, 3H), 3.75 (s, 3H), 4.01 (q, J=7.0 Hz, 2H), 5.57 (br s, 2H), 6.71 (d, J=1.7 Hz, 1H), 7.03 (d, J=1.7 Hz, 1H). 13C NMR (75 MHz, DMSO): δ 14.51, 52.09, 64.31, 100.87, 108.93, 110.33, 128.52, 145.93, 154.51, 166.10. MS (ISP): 230.0 [M+H]+.

후처리

  1. additionAfter the addition
  2. customwas removed
  3. concentrationThe solution was concentrated by evaporation under reduced pressure
  4. extractionthe solution extracted with ethyl acetate (3×100 mL)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. customthe solvent removed by evaporation under reduced pressure
  7. customthe crude material purified by recrystallization from dichloromethane yielding 0.88 g (100%) of the title compound

출처 및 근거

ORD 기록
ord-ba52e64bb49c45258447681b1f53b957
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645753B2

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