Sodium Hydroxide → HCID 71087699, compound

HRID 1478895Notes

Reaction equation

HRID 1478895 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([C:12]([O:14]C)=[O:13])[N:8]=[CH:7][C:6]=2[C:5]([CH3:16])=[CH:4]1)[CH3:2].[OH-].[Na+]>C1COCC1>[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[N:8]=[CH:7][C:6]=2[C:5]([CH3:16])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71087757HCID 71087757, compound

Product 1

HCID 71087699HCID 71087699, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 200-ml round bottom flask, methyl 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1N, 6.0 g, 28 mmol) was dissolved in THF (50 ml). To the mixture was added a 2M NaOH (28 ml, 55 mmol) solution. The reaction was stirred at room temperature for 3 hrs. After completion, volatiles were removed and the residue was cooled in an ice bath and neutralized with dilute HCl to pH=4.0-4.5. The aqueous mixture washed with ethyl acetate (2×100 ml) and then lyophilized to give the crude product 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (10) which is used in the next step without further purification.

Workup

  1. customAfter completion, volatiles were removed
  2. temperaturethe residue was cooled in an ice bath
  3. washThe aqueous mixture washed with ethyl acetate (2×100 ml)

Sources & evidence

ORD record
ord-3c14028d769e4584ab8c145d6cd154f5
Source dataset
uspto-grants-2016_08
Patent number
US09403819B2

Reaction notes

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