Potassium Carbonate → 3-Amino-2-benzoyl-6-chloroindole

HRID 379722Notes

Reaction equation

HRID 379722 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4](C(OCC)=O)[C:3]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 183678333-Amino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

Product 1

HCID 183679723-Amino-2-benzoyl-6-chloroindoleYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of step 2 (4.5 g, 13 mmol) and K2CO3 (18 g, 130 mmol) was heated at reflux for 5 h in 50% aqueous ethanol. The mixture was cooled and concentrated, and the residue partitioned between water (50 ml) and dichloromethane (100 ml). The organic extract was dried (MgSO4) and solvent removed. The residual solid was recrystallized from hexane/ethyl acetate to afford 3.2 g (91%) of the title compound. m.p.: 128-130° C. 1H-NMR (CDC13) δ: 7.85-7.76 (2H, m), 7.64 (1H, br s), 7.59-7.49 (4H, m), 7.22 (1H, d, J=1.8 Hz), 7.02 (1H, dd, J=1.8, 8.4 Hz), 5.60 (2H, br s).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customthe residue partitioned between water (50 ml) and dichloromethane (100 ml)
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4) and solvent
  6. customremoved
  7. customThe residual solid was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-b361cae76bf14fbd8c85d118b0e8c4c1
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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