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

HRID 1094849Notes

Reaction equation

HRID 1094849 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 (magnesium 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, 3H).

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 (magnesium sulfate)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b2b67b22539844dbaec3bdbced409b6c
Source dataset
uspto-grants-2012_03
Patent number
US08133995B2

Reaction notes

Loading…