Methanol → methyl 5-cyano-1H-pyrrole-3-carboxylate

HRID 73656Notes

Reaction equation

HRID 73656 reaction equation
[CH3:1][O-:2].[Na+].ClC(Cl)(Cl)C([C:8]1[CH:9]=[C:10]([C:13]#[N:14])[NH:11][CH:12]=1)=O.[CH3:17][OH:18]>>[C:13]([C:10]1[NH:11][CH:12]=[C:8]([C:1]([O:18][CH3:17])=[O:2])[CH:9]=1)#[N:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 124151024-(trichloroacetyl)-1H-pyrrole-2-carbonitrile

Product 1

HCID 12415103methyl 5-cyano-1H-pyrrole-3-carboxylateYield 98%

Procedure

Sodium methoxide (17.8 g, 329 mmol) was added to a solution of 4-(trichloroacetyl)-1H-pyrrole-2-carbonitrile (39.0 g, 164 mmol) in methanol (350 mL). The reaction was stirred for 16 h and then the methanol was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (800 mL) and the solution was adjusted to pH 6 using 1 M hydrochloric acid. The layers were separated and then the organic layer was washed with water and brine, dried (magensium sulfate) and evaporated under reduced pressure to afford the expected product (24.2 g, 98%). 1H NMR (DMSO-d6) δ 7.76 (s, 1H), 7.28 (s, 1H), 3.72 (s, 3 H).

Workup

  1. customthe methanol was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (800 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried (magensium sulfate)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c56dfb14664047cbb609a367080ed4c3
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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