Chloral → 5-cyano-1-methyl-1H-pyrrole-2-acetic acid

HRID 1732557Notes

Reaction equation

HRID 1732557 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[O:7]=[CH:8][C:9](Cl)(Cl)Cl.[C-:13]#[N:14].[K+].C(=O)([O-])[O-].[K+].[K+].[OH-:22].[Na+]>O1CCOCC1.CO>[C:13]([C:6]1[N:2]([CH3:1])[C:3]([CH2:9][C:8]([OH:22])=[O:7])=[CH:4][CH:5]=1)#[N:14]

Participants

8

Reactant 5

HCID 6407ChloralHCID 73041-MethylpyrroleHCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 155715345-cyano-1-methyl-1H-pyrrole-2-acetic acidYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-Methylpyrrole (1.62 g, 20.0 mmol) and chloral (3.20 g, 21.7 mmol) were reacted in dioxane (5 ml) to afford the adduct. A solution of potassium cyanide (5.70 g, 88 mmol) and potassium carbonate (2.80 g, 20 mmol) dissolved in methanol (150 ml) was added to the adduct and the mixture was stirred for 4 days. Then sodium hydroxide (3.0 g, 75 mmol) was added portion-wise to the mixture for the next 3 days. The reaction mixture was worked-up in the same manner as described in Example 3 above to afford the desired product, 5-cyano-1-methylpyrrole-2-acetic acid (1.50 g).

Workup

  1. customto afford the adduct
  2. additionwas added to the adduct

Sources & evidence

ORD record
ord-213fbb723a2c4c3480ec4fb33e3ea4ab
Source dataset
uspto-grants-1980_12
Patent number
US04238396

Reaction notes

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