Sulfuric Acid → Methyl 3-amino-5-hydroxy-4-iodobenzoate

HRID 1990830

反応式

HRID 1990830 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:12])[C:10]=1[I:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[C:18](=O)([O-])O.[Na+]>CO>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([OH:12])[C:10]([I:11])=[C:2]([NH2:1])[CH:3]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 684584523-Amino-5-hydroxy-4-iodobenzoic acid

生成物 1

HCID 68458438Methyl 3-amino-5-hydroxy-4-iodobenzoate収率 33%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 3-amino-5-hydroxy-4-iodo-benzoic acid (0.20 g, 0.72 mmol, 1.0 equiv) in methanol (5 mL) was added conc. sulfuric acid (0.20 mL, 0.035 g, 0.36 mmol, 0.5 equiv) and the reaction mixture heated to reflux. After 2 h, the reaction mixture was poured on ice, the pH adjusted to 9 by addition of a sat. solution of sodium hydrogencarbonate and extracted with ethyl acetate (2×50 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 (1:1) providing 0.07 g (33%) of the title compound. 1H NMR (250 MHz, DMSO): δ 3.78 (s, 3H), 5.45 (br s, 2H), 6.68 (s, 1H), 6.85 (s, 1H), 10.32 (br s, 1H). MS (EI): 293.0 [M]+.

後処理

  1. temperaturethe reaction mixture heated to reflux
  2. additionthe reaction mixture was poured on ice
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-615f6a5a3c5c4591af5883cfb2829b49
出典データセット
uspto-grants-2010_01
特許番号
US07645753B2

関連ノート

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