Sodium Hydroxide → 5-chloro-2-methyl-1H-indole-7-carboxylic acid

HRID 855264Notes

Reaction equation

HRID 855264 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:15])[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([CH3:14])=[CH:10]2)=[O:4].[OH-].[Na+]>CO>[Cl:15][C:7]1[CH:8]=[C:9]2[C:13](=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1)[NH:12][C:11]([CH3:14])=[CH:10]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69347467HCID 69347467, compound

Product 1

HCID 693469145-chloro-2-methyl-1H-indole-7-carboxylic acidYield 73.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-chloro-2-methyl-1H-indole-7-carboxylic acid methyl ester (30 mg, 0.13 mmol) in MeOH (5 ml) was added 1N NaOH(aq) (268 μl, 0.27 mmol) and the reaction mixture was refluxed for 2 h. The reaction mixture was concentrated in vacuo and water was added. The aqueous layer was acidified to pH3 using 1N HCl and the aqueous layer was extracted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the desired product (20 mg, 71%) which did not require further purification. MS (ISP) 208.1 (M−H)−.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo and water
  3. additionwas added
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d07f739d2544cdb8b632e66c8d54710
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

Loading…