Ammonium formate → Ethyl 5-methyl-1H-pyrrole-3-carboxylate

HRID 1967413Notes

Reaction equation

HRID 1967413 reaction equation
Cl[C:2]1[NH:3][C:4]([CH3:12])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C([O-])=O.[NH4+]>[C].[Pd].C(O)C>[CH3:12][C:4]1[NH:3][CH:2]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11008659HCID 11008659, compound

Product 1

HCID 12586753Ethyl 5-methyl-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

10% palladium carbon (anhydrous) (2.5 g) was suspended with ethanol (500 mL) under argon gas atmosphere. Ethyl 2-chloro-5-methyl-1H-pyrrole-3-carboxylate (50 g; see, Tetrahedron Letters, Vol. 35, No. 33, 5989-5992 (1994)) and ammonium formate (51 g) were added to the reaction mixture at room temperature, and it was stirred at room temperature for 8 hours. The reaction mixture was subjected to filtration with Celite (trade name), the filtrate was concentrated under reduced pressure. Water and ethyl acetate were added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed by water and a saturated aqueous solution of sodium chloride, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate, to thereby obtain a title compound (40 g) having the following physical properties.

Workup

  1. filtrationThe reaction mixture was subjected to filtration with Celite (trade name)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater and ethyl acetate were added to the obtained residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed by water
  6. concentrationa saturated aqueous solution of sodium chloride, and concentrated under reduced pressure
  7. dry with materialafter drying with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-b7b1231543f044eb9f1864a3fe4fa98b
Source dataset
uspto-grants-2013_04
Patent number
US08420810B2

Reaction notes

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