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

HRID 2039968Notes

Reaction equation

HRID 2039968 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[C:11]([C:13]([O:15]C)=[O:14])[NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].C(O)C.[OH-].[Li+]>O>[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium 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 52.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask is charged successively with 5 g (22.62 mmol) of methyl 5-nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (Azasynth), 50 mL of 95% ethanol, 50 mL of water and 1.63 g (67.92 mmol) of lithium hydroxide. The reaction mixture is refluxed for 30 minutes and then left to return to room temperature. The solution is concentrated under reduced pressure and then diluted in 200 mL of water. The aqueous phase is extracted with 3×60 mL of ethyl acetate, then acidified with 32% hydrochloric acid until the pH is between 2 and 3. The precipitate formed is filtered, rinsed with 50 mL of ethyl acetate and then dried under vacuum for 6 h. 2.45 g of a white solid is obtained (52%).

Workup

  1. temperatureThe reaction mixture is refluxed for 30 minutes
  2. waitleft
  3. customto return to room temperature
  4. concentrationThe solution is concentrated under reduced pressure
  5. additiondiluted in 200 mL of water
  6. extractionThe aqueous phase is extracted with 3×60 mL of ethyl acetate
  7. customThe precipitate formed
  8. filtrationis filtered
  9. washrinsed with 50 mL of ethyl acetate
  10. customdried under vacuum for 6 h

Sources & evidence

ORD record
ord-8424beda1e0d48dc9f874f80b29a2961
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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