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

HRID 2364719노트

반응식

HRID 2364719 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3e646b25477c4414b2b8dccbf0b0d132
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691822B2

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