Formic Acid → Methyl 5-formylpyrrole-3-carboxylate

HRID 358349Notes

Reaction equation

HRID 358349 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:10]#N)[NH:8][CH:9]=1)=[O:4].C(O)=[O:13]>[Ni]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:10]=[O:13])[NH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 12415103methyl 5-cyano-1H-pyrrole-3-carboxylate

Product 1

HCID 579027Methyl 5-formylpyrrole-3-carboxylateYield 36%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

3.6 g (27 millimoles) of 2-cyanopyrrole-4-carboxylic acid methyl ester, 17 g of Raney nickel, and 450 ml of 75% formic acid are introduced, in a flask, into an oil bath preheated to 120° C. and made to react for one hour. Subsequently, the mixture is poured into 1 liter of ice water and repeatedly extracted with ether. After drying and concentration of the ether phase, 1.4 g (36% of theory) of 2-formylpyrrole-4-carboxylic acid methyl ester is obtained, mp 126° C.

Workup

  1. custompreheated to 120° C.
  2. customto react for one hour
  3. extractionrepeatedly extracted with ether
  4. customAfter drying

Sources & evidence

ORD record
ord-f2c0ece3562f4a1d8a949c5c44ee2063
Source dataset
uspto-grants-1984_08
Patent number
US04466976

Reaction notes

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