Methanol → 3-Amino-4-methylthiophene-2-carboxylic acid

HRID 1688072ノート

反応式

HRID 1688072 の反応式
[NH2:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([O:10]C)=[O:9].[OH-].[Na+].CO>O>[NH2:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([OH:10])=[O:9]

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 123584Methyl 3-amino-4-methylthiophene-2-carboxylate

生成物 1

HCID 149896783-Amino-4-methylthiophene-2-carboxylic acid収率 84.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of methyl 3-amino-4-methyl-2-thiophene carboxylate (5 g, 29 mmol) and sodium hydroxide (3.5 g, 88 mmol) in a mixed solution (methanol:H2O/30 ml:120 ml) was heated at 50° C. for over night. The solution was cooled to room temperature and extracted with methylene chloride. The aqueous phase was acidified with 6N HCl until pH equal to 5. The aqueous phase was extracted again with ethyl acetate, and solvent phase washed with brine and dried over by sodium sulfate. After filtered and dried over the solvent, evaporated solvent to give 3.85 g of 3-amino-4-methyl-thiophene-2-carboxylic acid as a white solid in 84% yield: 1H NMR (300 MHz, CDCl3) δ 7.05 (d, 1H), 3.12 (br, 2H), 2.16 (s, 3H); MS (m/e): 157.9 (M+1).

後処理

  1. extractionextracted with methylene chloride
  2. extractionThe aqueous phase was extracted again with ethyl acetate, and solvent phase
  3. washwashed with brine
  4. dry with materialdried over by sodium sulfate
  5. filtrationAfter filtered
  6. customdried over the solvent
  7. customevaporated solvent

出典と根拠

ORDレコード
ord-12a02a222cd7427cb0e49e819f666f5f
出典データセット
uspto-grants-2012_04
特許番号
US08148391B2

反応ノート

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