Nitric Acid → 3-Cyano-5-ethyl-1H-pyrrole-2-carboxylic acid

HRID 2233829Notes

Reaction equation

HRID 2233829 reaction equation
[CH2:1]([C:3]1[NH:7][C:6]([CH:8]=[O:9])=[C:5]([C:10]#[N:11])[CH:4]=1)[CH3:2].[N+]([O-])(O)=[O:13]>O.[OH-].[Na+].[N+]([O-])([O-])=O.[Ag+]>[C:10]([C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[NH:7][C:6]=1[C:8]([OH:13])=[O:9])#[N:11]

Participants

6

Reactant 2

HCID 944Nitric AcidHCID 86038366HCID 86038366, compound2×

Product 1

HCID 685798453-Cyano-5-ethyl-1H-pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

Silver nitrate (1.41 g, 8.3 mmol) in water (100 ml) was added to a solution of 5-ethyl-2-formyl-1H-pyrrole-3-carbonitrile (Intermediate 58) (819 mg, 5.53 mmol) in 1 N sodium hydroxide (100 ml) in the dark. The mixture was heated at 100° C. in the dark for 1 h. The reaction mixture was cooled to room temperature and acidified with 65% aqueous nitric acid. The yellow/brown solution was extracted with EtOAc, dried over sodium sulfate and concentrated in vacuo to give the title compound (600 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe yellow/brown solution was extracted with EtOAc
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76b24322e32148e9874479808000fcab
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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