Water → Ethyl [4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

HRID 1375137Notes

Reaction equation

HRID 1375137 reaction equation
[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][CH3:16])=[C:6]2[C:17]([O:19][C:20](=O)[C:5]=12)=[O:18])[CH3:2].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:25][CH:24]=1.O>C(O)(=O)C>[CH2:15]([O:14][C:7]1[C:6]2[C:17](=[O:18])[N:22]([C:23]3[CH:24]=[CH:25][C:26]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:27][CH:28]=3)[C:20](=[O:19])[C:5]=2[C:4]([O:3][CH2:1][CH3:2])=[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12)[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 225219p-Aminophenylacetic acid ethyl esterHCID 207619774,9-Bis(ethyloxy)naphtho[2,3-c]furan-1,3-dione

Product 1

HCID 20761976Ethyl [4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,4-Diethoxy-2,3-naphthalenedicarboxylic anhydride (23.3 g, 81.5 mmol) and ethyl (4-aminophenyl)acetate (14.8 g, 82 mmol) were refluxed under nitrogen in acetic acid (160 ml) overnight. The mixture was cooled to room temperature and poured into water (1 L). The white solid was filtered, washed with water and dissolved in dichloromethane (800 ml). The solution was washed with water, brine and dried (MgSO4) and the solvent evaporated under vacuum to give ethyl [4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate as an off-white solid, 33 g, 96%.

Workup

  1. filtrationThe white solid was filtered
  2. washwashed with water
  3. dissolutiondissolved in dichloromethane (800 ml)
  4. washThe solution was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-6325bd012b25457f9a39e144863bf72a
Source dataset
uspto-grants-2007_01
Patent number
US07166631B2

Reaction notes

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