Sodium Hydroxide → 4-[(Benzofuran-2-ylmethyl)amino]-phthalic acid

HRID 331538ノート

反応式

HRID 331538 の反応式
C[O:2][C:3](=[O:25])[C:4]1[C:5](=[CH:10][C:11]([NH:14][CH2:15][C:16]2[O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[CH:20]=2)=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[CH:20]=[C:16]1[CH2:15][NH:14][C:11]1[CH:10]=[C:5]([C:6]([OH:8])=[O:7])[C:4](=[CH:13][CH:12]=1)[C:3]([OH:25])=[O:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 67019667Dimethyl 4-[(1-benzofuran-2-ylmethyl)amino]phthalate

生成物 1

HCID 670196574-[(Benzofuran-2-ylmethyl)amino]-phthalic acid収率 98%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 4-[(benzofuran-2-ylmethyl)-amino]-phthalic acid dimethyl ester (0.89 g, 3.30 mmol) and 3N sodium hydroxide (50 mL) in ethanol (100 mL) was refluxed for one hour. The reaction mixture was cooled to room temperature, and the solvent was removed under vacuum. The residue was dissolved in water (100 mL), washed with CH2Cl2 (2×100 mL), and acidified (HCl). The resulting mixture was extracted with ethyl acetate (2×100 mL), and the combined organic layers were washed with water (2×100 mL), dried (MgSO4), and evaporated, providing 0.80 g of 4-[(benzofuran-2-ylmethyl)amino]-phthalic acid, in 98% yield; 1H NMR (DMSO-d6) δ 4.54 (d, J=4.5 Hz, 2H), 6.71-6.77 (m, 3H), 7.18-7.29 (m, 3H), 7.51-7.61 (m, 3H), 12.52 (br, 2H).

後処理

  1. temperaturewas refluxed for one hour
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in water (100 mL)
  4. washwashed with CH2Cl2 (2×100 mL)
  5. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  6. washthe combined organic layers were washed with water (2×100 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated

出典と根拠

ORDレコード
ord-10fc3ee0dcb148299aa74e703d522bbd
出典データセット
uspto-grants-2014_11
特許番号
US08877780B2

反応ノート

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