Sodium Hydroxide → 1-(ethoxymethyl)-1H-indole-4-carboxylic acid

HRID 1886736Notes

Reaction equation

HRID 1886736 reaction equation
[CH2:1]([O:3][CH2:4][N:5]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([C:14]([O:16]C)=[O:15])[C:8]=2[CH:7]=[CH:6]1)[CH3:2].[OH-].[Na+]>CO>[CH2:1]([O:3][CH2:4][N:5]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([C:14]([OH:16])=[O:15])[C:8]=2[CH:7]=[CH:6]1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67468002methyl 1-(ethoxymethyl)-1H-indole-4-carboxylate

Product 1

HCID 674641781-(ethoxymethyl)-1H-indole-4-carboxylic acidYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 1-(ethoxymethyl)-1H-indole-4-carboxylate (135 g, 0.58 mol) in methanol (2 L) is added aqueous sodium hydroxide (68 g, 1.74 mol in 340 mL of H2O). The reaction mixture is stirred at 50° C. for 3 h. The volatiles are removed in vacuo. The residue is acidified with HCl (2 M) until pH=3-4, then extracted with EA (2×700 mL). The combined extracts are washed with aqueous saturated sodium chloride (2×250 mL), dried over anhydrous Na2SO4, and concentrated to yield the title compound (123 g, 96%). MS (m/z): 220 (M+H)+.

Workup

  1. customThe volatiles are removed in vacuo
  2. extractionextracted with EA (2×700 mL)
  3. washThe combined extracts are washed with aqueous saturated sodium chloride (2×250 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d76d62db68f425aaad211621a0352d7
Source dataset
uspto-grants-2013_08
Patent number
US08501166B2

Reaction notes

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