Oxalic Acid → Methyl 1-methyl-5-(cyanohydroxyphenylmethyl)pyrrole-2-acetate

HRID 848041Notes

Reaction equation

HRID 848041 reaction equation
[C:1]([C:9]#[N:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][C:18]([O:20][CH3:21])=[O:19].C(O)(=O)C(O)=O>CCOCC>[CH3:11][N:12]1[C:16]([C:1]([C:9]#[N:10])([OH:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:15][CH:14]=[C:13]1[CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 11953PhenylglyoxylonitrileHCID 103992Methyl 1-methylpyrrol-2-acetate

Product 1

HCID 12940094Methyl 1-methyl-5-(cyanohydroxyphenylmethyl)pyrrole-2-acetateYield 12%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Benzoyl cyanide, 0.67 g (0.005 mole) and methyl 1-methylpyrrole-2-acetate, 0.76 g (0.005 mole) were stirred together in ether (2 ml) containing oxalic acid (0.04 g). The reaction was run in the dark at room temperature. After six days, the reaction mixture was placed in the freezer overnight, filtered, and washed with cold ether to yield 0.17 g (12 percent) of methyl 1-methyl-5-(cyanohydroxyphenylmethyl)pyrrole-2-acetate, mp 137°-8°. The solid state IR spectrum was identical to authentic material.

Workup

  1. customdark at room temperature
  2. customwas placed in the freezer overnight
  3. filtrationfiltered
  4. washwashed with cold ether

Sources & evidence

ORD record
ord-f28cd94c2cd240b29f9b55846bf16368
Source dataset
uspto-grants-1981_10
Patent number
US04294760

Reaction notes

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