Water → HCID 69659257, compound

HRID 1829041Notes

Reaction equation

HRID 1829041 reaction equation
[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][C:16]([CH2:20][CH2:21][CH2:22]OS(C)(=O)=O)=[CH:17][CH:18]=3)[CH2:13][O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.O>CN(C=O)C>[N:28]1([CH2:22][CH2:21][CH2:20][C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[C:11](=[C:10]2[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[NH:3][C:2]2=[O:1])[O:12][CH2:13]3)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 72382356HCID 72382356, compound

Product 1

HCID 69659257HCID 69659257, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methanesulfonic acid 3-[1-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-5-yl]-propyl ester (400 mg, 1.04 mmol) and morpholine (1.5 ml, 17.2 mmol) in DMF (5 ml) was heated at 90° C. for 1.5 hours. The mixture was cooled, and poured into water (125 ml) with stirring. The solid was filtered, washed with water and dried under vacuum to give 3-[5-(3-morpholin-4-yl-propyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a yellow solid (385 mg, 98%).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d3df8d8cf86548c482826d8015c18540
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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