Hydrochloric Acid → 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one

HRID 640847Notes

Reaction equation

HRID 640847 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10](=[O:20])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH:21](C([O-])=O)[C:22]([O-:24])=O)([O-])=O.Cl>CCO.C(Cl)(Cl)Cl>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([C:8]2[CH:9]=[C:4]3[C:5]([CH2:21][C:22](=[O:24])[NH:1]3)=[CH:6][CH:7]=2)=[O:20])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86610376[2-Nitro-4-(4-nitrobenzoyl)phenyl]malonate

Product 1

HCID 592564856-(4-Amino-benzoyl)-1,3-dihydro-indol-2-oneYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

[2-Nitro-4-(4-nitrobenzoyl)phenyl]malonate (4.15 g, 9.61 mmol) was dissolved in EtOH (24 mL) after which Sn powder (9.16 g, 77 mmol) was added followed by dropwise addition of concentrated HCl(aq) (26 mL). The reaction mixture was allowed to reflux for 3 hours, filtered while hot and then allowed to cool to room temperature. The cooled reaction mixture was diluted with CHCl3 (400 mL) and then extracted once with H2O (400 mL). The aqueous layer was then neutralized with NaHCO3 (pH=7) and then extracted with a 95% EtOAc/5% i-prOH solution (3×400 mL). The organic layers were combined and dried over anhydrous Na2SO4. The solution was then concentrated in vacuo affording the 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one in 51% yield (1.24 g, 4.90 mmol).

Workup

  1. additionwas added
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered while hot and
  4. customThe cooled reaction mixture
  5. extractionextracted once with H2O (400 mL)
  6. extractionextracted with a 95% EtOAc/5% i-prOH solution (3×400 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationThe solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-17e3b2bf357f4e348f7dbabe64c50af6
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

Loading…