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

HRID 18932

Reaction equation

HRID 18932 reaction equation
[C:1]([C:5]1[NH:9][C:8]([C:10]([O:12]C)=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>O.C1COCC1.CO>[C:1]([C:5]1[NH:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18322358methyl 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylate

Product 1

HCID 183223915-tert-butyl-3-nitro-1H-pyrrole-2-carboxylic acidYield 64.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A solution of LiOH monohydrate (0.083 g, 2.0 mmol) in water (1 mL) was added to a solution of methyl 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylate (0.150 mL, 0.66 mmol) in THF:MeOH (3:1, 3 mL) and the resulting mixture heated at 75° C. for 5 hours. The reaction was cooled down to room temperature and acidified with 1N aqueous HCl, extracted with ethyl acetate. The combined organic layers were dried, the solvent eliminated under vacuum and the crude product recrystallized from dichloromethane:hexane to afford 90 mg of expected 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylic acid as a yellow solid.

Workup

  1. temperatureThe reaction was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe combined organic layers were dried
  4. customthe crude product recrystallized from dichloromethane

Sources & evidence

ORD record
ord-7453776a39e54e01a5ebd772ea3e57f2
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Linked notes

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