Sodium Hydroxide → 2,3-Dimethyl-1H-indole-5-carboxylic acid

HRID 2170620Notes

Reaction equation

HRID 2170620 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14]CC)=[O:13])=[CH:6][CH:5]=2.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([OH:14])=[O:13])=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 612460Ethyl 2,3-dimethyl-1H-indole-5-carboxylate

Product 1

HCID 6933862,3-Dimethyl-1H-indole-5-carboxylic acidYield 114.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2,3-dimethyl-1H-indole-5-carboxylate (500 mg, 2.3 mmol) in ethanol (10 mL) was added a 5N NaOH solution (9.2 mL). The resulting solution was heated at 50° C. for 4 h, and then quenched carefully by addition of a 6N HCl solution (10 mL). The mixture was diluted with ethyl acetate, washed with a 0.5 N HCl solution and brine, dried on MgSO4, and concentrated to afford a yellow powder (500 mg, 100%). ESI-MS (m/z): 190 [MH]+

Workup

  1. customquenched carefully by addition of a 6N HCl solution (10 mL)
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with a 0.5 N HCl solution and brine
  4. customdried on MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-759c3bb354fd4a8dbee2d1e89c965e12
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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