Sodium Hydroxide → HCID 67019688、化合物

HRID 63397ノート

反応式

HRID 63397 の反応式
C[O:2][C:3](=[O:21])[C:4]1[C:5](=[CH:10][C:11]([NH:14][CH2:15][C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[O:17]1[CH:18]=[CH:19][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:21])=[O:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 67019694Dimethyl 4-[(2-furylmethyl)amino]phthalate

生成物 1

HCID 67019688HCID 67019688、化合物収率 44%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 4-[(furan-2-ylmethyl)-amino]-phthalic acid dimethyl ester (1.11 g, 3.84 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 organic phase was washed with water (2×100 mL), and dried (MgSO4) and evaporated. The resulting solid was stirred in ether for 2 hours. The solid was filtered to give the 0.44 g of 4-[(furan-2-ylmethyl)-amino]-phthalic acid, in 44% yield; 1H NMR (DMSO-d6) δ 4.33 (d, J=5.1 Hz, 2H), 6.31 (d, J=3.0 Hz, 1H), 6.39 (dd, J=3.0 Hz, 1.8 Hz, 1H), 6.65-6.71 (m, 2H), 7.00 (t, J=5.7 Hz, 1H), 7.57-7.60 (m, 2H), 12.51 (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 organic phase was washed with water (2×100 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. filtrationThe solid was filtered

出典と根拠

ORDレコード
ord-f32cf060239a41329bf4aa5f9b25877d
出典データセット
uspto-grants-2016_09
特許番号
US09447070B2

反応ノート

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