Hydrochloric Acid → 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-

HRID 217956Notes

Reaction equation

HRID 217956 reaction equation
C([O:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:8]=1)=[O:6])CC.[OH-].[Na+].Cl>C(O)C>[C:19]([N:9]1[C:10]2=[N:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[C:15]2[C:7]([C:5]([OH:6])=[O:4])=[CH:8]1)([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669245181H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-, propyl ester

Product 1

HCID 669243961H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-Yield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5.00 g (16.38 mmol) of 1-tert-butyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid propyl ester in 50 mL of 95° ethanol, it was added 2M NaOH (50 mL; 100 mmol) under stirring. The mixture was heated to reflux for 1 hour obtaining the complete consumption of the substrate. The resulting solution was cooled to room temperature and concentrated under reduced pressure to a slurry that was diluted with 250 mL of water and washed with 100 mL of a 1:1 mixture of diethyl ether and ethyl acetate. The aqueous layer was treated with 5M HCl (37 mL; 185 mmol) under efficient stirring at room temperature. The precipitate was filtered off, washed twice with 10 mL of water and dried so as to afford 3.84 g of the title compound as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customobtaining
  4. customthe complete consumption of the substrate
  5. concentrationconcentrated under reduced pressure to a slurry that
  6. additionwas diluted with 250 mL of water
  7. washwashed with 100 mL of a 1:1 mixture of diethyl ether and ethyl acetate
  8. stirringunder efficient stirring at room temperature
  9. filtrationThe precipitate was filtered off
  10. washwashed twice with 10 mL of water
  11. customdried so as

Sources & evidence

ORD record
ord-2dd0100a063c48ccb5ac3b9f6b2acc81
Source dataset
uspto-grants-2012_06
Patent number
US08198298B2

Reaction notes

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