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 222432노트

반응식

HRID 222432 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b1428b02837a464a93fa45c270bb4bce
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207213B2

반응 노트

불러오는 중…