6-Amino-5-fluoroindolin-2-one → HCID 10040435, compound

HRID 1655835Notes

Reaction equation

HRID 1655835 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[F:12].[C:13]1(=O)[O:18][C:16](=[O:17])[CH:15]2[CH2:19][CH2:20][CH:21]=[CH:22][CH:14]12.C(OCC)(=O)C.C(Cl)Cl>C(O)(=O)C>[F:12][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[N:1]1[C:13](=[O:18])[C:14]3[CH2:22][CH2:21][CH2:20][CH2:19][C:15]=3[C:16]1=[O:17])[NH:8][C:7](=[O:11])[CH2:6]2

Participants

5

Reactant 3

HCID 101035046-Amino-5-fluoroindolin-2-oneHCID 127266013a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dioneHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 10040435HCID 10040435, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6-amino-5-fluoro-2-indolinone (10.5 g, 63.25 mmol) and tetrahydrophthalic anhydride (10.95 g, 66.42 mmol) in acetic acid (30 mL) is heated at reflux for 2 hours, cooled and concentrated in vacuo to obtain a residue. Chromatography of the residue using silica gel and a 3:7 ethyl acetate/methylene chloride solution gives the title product as a light violet solid (14.7 g, mp 234°-236° C.). Following the procedure of Example 3, but substituting 6-amino-2-indolinone for 6-amino-5-fluoro-2-indolinone gives N-(2-oxo-6-indolinyl)-1-cyclohexene-1,2-dicarboximide as a green solid, mp 225°-226° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-f6a0bc7d6ce9416bb7c9ddc7b300db3c
Source dataset
uspto-grants-1993_10
Patent number
US05252536

Reaction notes

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