p-Aminophenylacetic acid ethyl ester → Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

HRID 222432ノート

反応式

HRID 222432 の反応式
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([C:22](O)=[O:23])[C:5]=1[C:25](O)=[O:26])[CH3:2].[CH2:28]([O:30][C:31](=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=1)[CH3:29]>C(O)(=O)C.[Cl-].[Na+].O>[CH2:28]([O:30][C:31](=[O:40])[CH2:32][C:33]1[CH:34]=[CH:35][C:36]([N:39]2[C:22](=[O:23])[C:6]3[C:7]([O:14][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]4=[C:4]([O:3][CH2:1][CH3:2])[C:5]=3[C:25]2=[O:26])=[CH:37][CH:38]=1)[CH3:29]

参加物

5

反応物 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 580124801-(Ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid

生成物 1

HCID 58017612Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate収率 74.2%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A mixture of 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid (2.55 g, 6.97 mmol) and ethyl(4-aminophenyl)acetate (2.49 g, 13.9 mmol) were heated to 120° C. in acetic acid (20 ml) for 18 hours. The reaction mixture was diluted with brine and extracted with ethyl acetate twice. Combined organics were washed with water then dried over magnesium sulphate, the solvent evaporated to give a brown oil. This was purified by chromatography on silica gel, eluting with ethyl acetate (0-30%) in hexane to give the title compound as a peach coloured solid (2.63 g, 5.17 mmol). LC/MS: Rt=3.95, [MH]+ 510.

後処理

  1. extractionextracted with ethyl acetate twice
  2. washCombined organics were washed with water
  3. dry with materialthen dried over magnesium sulphate
  4. customthe solvent evaporated
  5. customto give a brown oil
  6. customThis was purified by chromatography on silica gel
  7. washeluting with ethyl acetate (0-30%) in hexane

出典と根拠

ORDレコード
ord-b1428b02837a464a93fa45c270bb4bce
出典データセット
uspto-grants-2012_06
特許番号
US08207213B2

反応ノート

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