Sodium Hydroxide → 6-Chloro-2-(4-chlorobenzoyl)indol-3-acetic acid

HRID 396421Notes

Reaction equation

HRID 396421 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH2:4][C:3]([OH:24])=[O:2])=[C:6]([C:15](=[O:23])[C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[NH:7]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9906983HCID 9906983, compound

Product 1

HCID 97983746-Chloro-2-(4-chlorobenzoyl)indol-3-acetic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl[6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl]acetate (Example 8, 1.80 g) and 2N aqueous NaOH (7.5 ml) in MeOH-THF (10 ml-10 ml) was stirred at 80° C. for 1 h. The mixture was cooled and concentrated. The residue was dissolved in water (150 ml) and washed with diethyl ether (50 ml). The aqueous layer was acidified with 2N aqueous HCl (10 ml), and extracted with ethyl acetate (100 ml×2). The combined organic extracts were washed with brine (50 ml), dried (MgSO4), and concentrated. The residual solids were recrystalized from toluene to afford 1.58 g (91%) of the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in water (150 ml)
  4. washwashed with diethyl ether (50 ml)
  5. extractionextracted with ethyl acetate (100 ml×2)
  6. washThe combined organic extracts were washed with brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residual solids were recrystalized from toluene

Sources & evidence

ORD record
ord-e3f5642825574b27b621e57f37b843da
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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