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

HRID 913165Notes

Reaction equation

HRID 913165 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.[NH2:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:36][C:35]=1[Cl:46].O>CN(C1C=CN=CC=1)C.C(O)(=O)C>[Cl:46][C:35]1[CH:36]=[C:37]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:38]=[CH:39][C:34]=1[N:33]1[C:27](=[O:28])[C:11]2[C:12]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]3=[C:9]([O:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:10]=2[C:30]1=[O:31]

Participants

6

Reactant 3

HCID 962WaterHCID 4380201,4-Bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acidHCID 17859298(4-Amino-3-chloro-phenyl)-acetic acid ethyl ester

Product 1

HCID 58012507Ethyl (3-chloro-4-{1,3-dioxo-4,9-bis[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1 1,4-bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid (5.0 g, 11.68 mmol), ethyl (4-amino-3-chlorophenyl)acetate (4.74 g, 22.2 mmol) and DMAP (0.427 g, 3.59 mmol) were heated to 120° C. in acetic acid (20 ml) for 18 hours. Water was added and the mixture and resulting brown solid collected by filtration and washed with water. This was triturated with ether to give a cream solid which was collected by filtration and dried in the vacuum oven (5.34 g, 8.83 mmol). LC/MS: Rt=4.15, [MH]+ 606.

Workup

  1. customthe mixture and resulting brown solid
  2. filtrationcollected by filtration
  3. washwashed with water
  4. customThis was triturated with ether
  5. customto give a cream solid which
  6. filtrationwas collected by filtration
  7. customdried in the vacuum oven (5.34 g, 8.83 mmol)

Sources & evidence

ORD record
ord-8fb15f0916914c888de841fe27f189db
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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