1-(Ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid → Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetate

HRID 913176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913176
[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].[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][C:30]=1[F:41]>CN(C1C=CN=CC=1)C.C(O)(=O)C>[CH2:1]([O:3][C:4]1[C:5]2[C:25](=[O:26])[N:28]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][C:30]=3[F:41])[C:22](=[O:23])[C:6]=2[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=12)[CH3:2]

Komponenten

5

Edukt 2

HCID 580124801-(Ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acidHCID 59760056Ethyl 2-(4-amino-3-fluorophenyl)acetate

Produkt 1

HCID 58012495Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetateAusbeute 110,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid (1.40 g, 3.32 mmol), ethyl (4-amino-3-fluorophenyl)acetate (1.24 g, 6.30 mmol) and DMAP (0.121 g, 0.995 mmol) were heated to 120° C. in acetic acid (20 ml) for 6 hours. The reaction mixture was triturated with water and the resulting yellow solid was collected by filtration and dried in the vacuum oven to give the title compound (1.93 g, 3.66 mmol). LC/MS: Rt=3.95, [MH]+ 528.

Aufarbeitung

  1. customThe reaction mixture was triturated with water
  2. filtrationthe resulting yellow solid was collected by filtration
  3. customdried in the vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-ace76eda108b4092a6d51759b9917686
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026270B2

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