Water → Ethyl (4-{1,3-dioxo-4,9-bis[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

HRID 222426Notes

Reaction equation

HRID 222426 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:11]([C:27](O)=[O:28])[C:10]=2[C:30](O)=[O:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:33]([O:35][C:36](=[O:45])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=1)[CH3:34].O>C(O)(=O)C>[CH2:33]([O:35][C:36](=[O:45])[CH2:37][C:38]1[CH:39]=[CH:40][C:41]([N:44]2[C:27](=[O:28])[C:11]3[C:12]([O:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]4=[C:9]([O:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:10]=3[C:30]2=[O:31])=[CH:42][CH:43]=1)[CH3:34]

Participants

5

Reactant 3

HCID 962WaterHCID 225219p-Aminophenylacetic acid ethyl esterHCID 4380201,4-Bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid

Product 1

HCID 58231481Ethyl (4-{1,3-dioxo-4,9-bis[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetateYield 99.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1,4-bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid (2.0 g, 4.67 mmol) and ethyl(4-aminophenyl)acetate (1.67 g, 9.35 mmol) were heated to 120° C. in acetic acid (30 ml) for 2 hours. The mixture solidified on standing at room temperature overnight. Water was added and the solid collected by filtration and washed with water. This was dried under vacuum to give the title compound (2.65 g, 4.64 mmol). LC/MS: Rt=4.24, [MH]+ 572.

Workup

  1. filtrationthe solid collected by filtration
  2. washwashed with water
  3. customThis was dried under vacuum

Sources & evidence

ORD record
ord-f514f9ab87a6436f8d355b5bdefe57ed
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

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