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

HRID 640884Notes

Reaction equation

HRID 640884 reaction equation
C([O:3][C:4](=O)[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=2)=[CH:13][C:12]=1[N+:28]([O-])=O)C(OCC)=O)C.Cl>CCO>[NH2:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[C:17]([C:14]1[CH:13]=[C:12]2[C:11]([CH2:5][C:4](=[O:3])[NH:28]2)=[CH:16][CH:15]=1)=[O:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59256487Diethyl 2-(2-nitro-4-(3-nitrobenzoyl)phenyl)malonate

Product 1

HCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-oneYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[2-Nitro-4-(3-nitro-benzoyl)-phenyl]-malonic acid diethyl ester (2.00 g, 4.65 mmol) was dissolved in EtOH (11.5 mL) after which Sn powder (4.42 g, 37.2 mmol) was added followed by dropwise addition of concentrated HCl(aq) (13 mL). The mixture was allowed to reflux for 3 hours, filtered while hot and then allowed to cool to room temperature. The mixture was diluted with CHCl3 (200 mL) and then extracted once with H2O (200 mL). The aqueous layer was then neutralized with NaHCO3 (pH=7) and then the aqueous layer was extracted with a 95% EtOAc/5% i-prOH solution (3×200 mL). The organic layers were combined and dried over anhydrous Na2SO4. The solution was then concentrated in vacuo affording the 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one in 44% yield (0.516 g, 2.05 mmol).

Workup

  1. additionwas added
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered while hot and
  4. additionThe mixture was diluted with CHCl3 (200 mL)
  5. extractionextracted once with H2O (200 mL)
  6. extractionthe aqueous layer was extracted with a 95% EtOAc/5% i-prOH solution (3×200 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationThe solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-70556b712ad747919166a9fabfb1aea1
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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