Sodium Hydroxide → HCID 71087699, compound

HRID 2405082Notes

Reaction equation

HRID 2405082 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 (1O) 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-cd24699dac754b34880ab939ae009daf
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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