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

HRID 346708Notes

Reaction equation

HRID 346708 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>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][C:26]1[CH:25]=[CH:24][C:23]([N:22]2[C:20](=[O:19])[C:5]3[C:4]([O:3][CH2:1][CH3:2])=[C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]4=[C:7]([O:14][CH2:15][CH3:16])[C:6]=3[C:17]2=[O:18])=[CH:28][CH:27]=1)[CH3:34]

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 the title compound 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-f1707a4238e6403fa1c728c098a0e1f6
Source dataset
uspto-grants-2007_02
Patent number
US07173047B2

Reaction notes

Loading…