Water → 7-Amino-2,3-dihydrobenzofuran-4-carboxylic acid

HRID 2364719ノート

反応式

HRID 2364719 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([O:13]C)=[O:12])=[C:6]2[C:10]=1[O:9][CH2:8][CH2:7]2.[OH-].[Li+].O>CO.O1CCCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([OH:13])=[O:12])=[C:6]2[C:10]=1[O:9][CH2:8][CH2:7]2

参加物

6

反応物 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68107686Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate

生成物 1

HCID 249683367-Amino-2,3-dihydrobenzofuran-4-carboxylic acid収率 80%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate 1g (2.30 g, 11.90 mmol) was dissolved in 80 mL of the mixture solvent of methanol and tetrahydrofuran (V/V=1:1) followed by the addition of a 1 M solution of lithium hydroxide solution (47.6 mL, 47.60 mmol) in tetrahydrofuran. The reaction solution was heated to reflux for 5 hours, then cooled down to room temperature, stirred for 12 hours. The reaction solution was added with 20 mL of water and concentrated under reduced pressure. The resulting residue was added with 100 mL of water, extracted with ethyl acetate (50 mL×2), the combined aqueous phase was added dropwise with 1 M hydrochloric acid to adjust pH to 3 resulting in the formation of precipitate. The precipitate was filtered to obtain the title compound 7-amino-2,3-dihydrobenzofuran-4-carboxylic acid 22e (1.70 g, yield: 80.0%) as a gary solid.

後処理

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 5 hours
  3. concentrationconcentrated under reduced pressure
  4. additionThe resulting residue was added with 100 mL of water
  5. extractionextracted with ethyl acetate (50 mL×2)
  6. additionthe combined aqueous phase was added dropwise with 1 M hydrochloric acid
  7. filtrationThe precipitate was filtered

出典と根拠

ORDレコード
ord-3e646b25477c4414b2b8dccbf0b0d132
出典データセット
uspto-grants-2014_04
特許番号
US08691822B2

反応ノート

読み込み中…