Isatoic Anhydride → HCID 69511859, compound

HRID 969669Notes

Reaction equation

HRID 969669 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:15])([CH3:14])[CH2:7][N:8]2[C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1.[C:16]12[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:21]C(=O)O[C:17]2=[O:18].C([O-])(O)=O.[Na+]>CS(C)=O>[C:11]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:17](=[O:18])[C:16]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH2:21])[CH:10]=2)[C:6]([CH3:15])([CH3:14])[CH2:7]1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 516892Sodium BicarbonateHCID 218651761-(6-Amino-3,3-dimethylindolin-1-yl)ethanone

Product 1

HCID 69511859HCID 69511859, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-(6-amino-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone (1.02 g, 5 mmol) and isatoic anhydride (0.85 g, 5.2 mmol) in DMSO (5 mL) was heated to 150° C. for 6 h. After cooling to RT, the mixture was suspended in a NaHCO3 solution (40 mL) and extracted with CH2Cl2 (20 mL×3). The organic solution was combined and concentrated in vacuo. The residue was purified via flash chromatography on silica gel (EtOAc:hexanes 9:2) to give the desired compound as an off-white solid.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with CH2Cl2 (20 mL×3)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified via flash chromatography on silica gel (EtOAc:hexanes 9:2)

Sources & evidence

ORD record
ord-8ba2bfa6ffe34cc4880925bb6281b67a
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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