Iodoethane → 3-Amino-5-ethoxy-4-iodo-benzoic acid methyl ester

HRID 1990831

반응식

HRID 1990831 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([I:11])=[C:6]([NH2:12])[CH:5]=1.[CH2:14](I)[CH3:15].CC(C)([O-])C.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH2:14][CH3:15])[C:7]([I:11])=[C:6]([NH2:12])[CH:5]=1

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 23676156Sodium t-butoxideHCID 68458438Methyl 3-amino-5-hydroxy-4-iodobenzoate

생성물 1

HCID 684595793-Amino-5-ethoxy-4-iodo-benzoic acid methyl ester수율 69.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-amino-5-hydroxy-4-iodo-benzoic acid methyl ester (0.25 g, 0.85 mmol, 1.0 equiv) in DMF (3 mL) and ethyl iodide (0.10 mL, 0.146 g, 0.94 mmol, 1.1 equiv) at 0° C. was added sodium tert-butoxide (0.11 g, 0.94 mmol, 1.1 equiv) in small portions over a time period of 10 min. After stirring for 1 h, the cooling bath was removed and the the reaction mixture stirred at rt for an additional 18 h. The solution was concentrated by evaporation under reduced pressure and extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over MgSO4, concentrated by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1) yielding 0.19 g (69%) of the title compound. 1H NMR (250 MHz, CDCl3): δ 1.49 (t, J=7.0 Hz, 3H), 3.89 (s, 3H), 4.11 (q, J=7.0 Hz, 2H), 4.33 (br s, 2H), 6.82 (d, J=2.7 Hz, 1H), 7.07 (d, J=2.7 Hz, 1H). MS (EI): 321.0 [M]+.

후처리

  1. customthe cooling bath was removed
  2. stirringthe the reaction mixture stirred at rt for an additional 18 h
  3. concentrationThe solution was concentrated by evaporation under reduced pressure
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-0b0c52acce7342a5a4a7a0aa9ec4465f
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645753B2

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