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

HRID 1990831ノート

反応式

HRID 1990831 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-0b0c52acce7342a5a4a7a0aa9ec4465f
出典データセット
uspto-grants-2010_01
特許番号
US07645753B2

反応ノート

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