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 222432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222432
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 58017612Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetateAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b1428b02837a464a93fa45c270bb4bce
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207213B2

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