Sodium Hydroxide → HCID 84655455, compound

HRID 1478894Notes

Reaction equation

HRID 1478894 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([C:11]([O:13]C)=[O:12])[N:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1.[OH-].[Na+]>CO.[Cl-].[Na+].O>[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([C:11]([OH:13])=[O:12])[N:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86674844HCID 86674844, compound

Product 1

HCID 84655455HCID 84655455, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

In a 500 mL pear flask was added methyl 1-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1B, 14 g, 71 mmol) in methanol (71.0 ml). At 0° C. was added 1N sodium hydroxide solution (140 ml, 140 mmol). This was then stirred at 0° C. for 1 h, when the reaction was complete. Brine (25 ml) was added and methanol was removed in vacuo. The aqueous mixture was washed twice with EtOAc. The aqueous layer was then acidified to pH 4; the resulting precipitate was collected on a fritted glass funnel and dried overnight under a stream of nitrogen to give the desired product 1-methyl-1H -pyrrolo[3,2-c]pyridine-6-carboxylic acid (1C, 10 g, 83% yield) as an off white powder. This was used in next step without further purification.

Workup

  1. custommethanol was removed in vacuo
  2. washThe aqueous mixture was washed twice with EtOAc
  3. customthe resulting precipitate was collected on a fritted glass funnel
  4. customdried overnight under a stream of nitrogen

Sources & evidence

ORD record
ord-e8019b4abca249afb374208a3e16ca63
Source dataset
uspto-grants-2016_08
Patent number
US09403819B2

Reaction notes

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