Hydrochloric Acid → 5-Nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

HRID 1478133Notes

Reaction equation

HRID 1478133 reaction equation
C[O:2][C:3]([C:5]1[NH:16][C:8]2=[N:9][CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=[C:7]2[CH:6]=1)=[O:4].[OH-].[K+].Cl>CO.O>[N+:13]([C:11]1[CH:12]=[C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[NH:16][C:8]2=[N:9][CH:10]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 40154011Methyl 5-nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 401519725-Nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

5-Nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester (6 g, 27.1 mmoles) was dissolved in methanol/water mixture (1/1). Potassium hydroxide (3 eq) was added and the mixture was heated at reflux overnight. After cooling down, the mixture was acidified until pH=3 by hydrochloric acid 3N. The precipitate was filtered off, washed with water, then diethyl ether, and dried under vacuum. A brownish solid, 5-nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid, is obtained (5.47 g). Yield=98%. ESI-MS: m/z 208 ([M+H]+). HPLC purity: 100%

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling down
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. dry with materialdiethyl ether, and dried under vacuum

Sources & evidence

ORD record
ord-6a950e1641184a5796b745d7254cb863
Source dataset
uspto-grants-2016_08
Patent number
US09403823B2

Reaction notes

Loading…