Water → HCID 69659375, compound

HRID 1829045Notes

Reaction equation

HRID 1829045 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[C:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]1=[O:23])[O:9][CH2:8]2.[C:24](OC(=O)C)(=[O:26])[CH3:25].O>C1COCC1.CN(C)C1C=CN=CC=1>[O:23]=[C:15]1[C:14](=[C:10]2[C:11]3[C:7](=[CH:6][C:5]([NH:4][CH2:3][CH2:2][O:1][C:24](=[O:26])[CH3:25])=[CH:13][CH:12]=3)[CH2:8][O:9]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 69659274HCID 69659274, compound

Product 1

HCID 69659375HCID 69659375, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 3-[5-(2-hydroxy-ethylamino)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one (50 mg, 0.16 mmol) and acetic anhydride (20 mg, 0.20 mmol) in THF (3 ml), was added 4-dimethylaminopyridine (10 mg, 0.08 mmol). The mixture was stirred for 30 minutes and was then poured into water (75 ml). The solid was filtered, washed with water and dried under vacuum to give acetic acid 2-[1-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-5-ylamino]-ethyl ester as a yellow solid (39 mg, 68%).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-306c52debeb64602b3bc01690a7e5835
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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