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

HRID 982698Notes

Reaction equation

HRID 982698 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]acetateYield 96%

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-92c2a00dc27946c385d5f14e04f5f6d6
Source dataset
uspto-grants-2005_03
Patent number
US06861441B1

Reaction notes

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