Hydrochloric Acid → 5-tert-butyl-2-nitro-1H-pyrrole-3-carboxylic acid

HRID 18935Notes

Reaction equation

HRID 18935 reaction equation
[C:1]([C:5]1[NH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:7]([C:13]([O:15]C)=[O:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>>[C:1]([C:5]1[NH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:7]([C:13]([OH:15])=[O:14])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59345806HCID 59345806, compound

Product 1

HCID 586792985-tert-butyl-2-nitro-1H-pyrrole-3-carboxylic acidYield 89%

Conditions

Temperature
80 °C

Procedure

To methyl 5-tert-butyl-2-nitro-1H-pyrrole-3-carboxylate (900 mg, 3.98 mmol) was added 12% aqueous KOH (5 mL), and the resulting reaction mixture was stirred at 80° C. for 30 min. The reaction mixture was poured into 1N aqueous HCl (excess), the aqueous phase was extracted 3 times with dichloromethane, the combined organic layers was dried and concentrated under vacuum to afford 5-tert-butyl-2-nitro-1H-pyrrole-3-carboxylic acid (5) as yellow solid (750 mg, 89%).

Workup

  1. customthe resulting reaction mixture
  2. extractionthe aqueous phase was extracted 3 times with dichloromethane
  3. customthe combined organic layers was dried
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7ecb447ff65f4a72941e0cbdcdcc8e86
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Reaction notes

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