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

HRID 848039Notes

Reaction equation

HRID 848039 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].ClC(Cl)(Cl)C(O)=O>CCOCC>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:13]1[N:12]([CH3:11])[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]=1

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 11953PhenylglyoxylonitrileHCID 103992Methyl 1-methylpyrrol-2-acetate

Product 1

HCID 12940094Methyl 1-methyl-5-(cyanohydroxyphenylmethyl)pyrrole-2-acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 6.7 g (0.05 mole) of benzoylcyanide, 7.6 g (0.05 mole) of methyl 1-methylpyrrole-2-acetate and 0.2 g of trichloroacetic acid in 20 ml. of ether was stirred for four days at 25° C. under argon. The solution was cooled to 0° and the solid methyl 5-(cyanohydroxyphenylmethyl)-1-methylpyrrole-2-acetate was collected by filtration; mp 148°-153°, yield, 4.0 g (28 percent).

Workup

  1. temperatureThe solution was cooled to 0°
  2. filtrationthe solid methyl 5-(cyanohydroxyphenylmethyl)-1-methylpyrrole-2-acetate was collected by filtration
  3. custommp 148°-153°, yield

Sources & evidence

ORD record
ord-86409ac2f2464fd09f1ef5b712719c46
Source dataset
uspto-grants-1981_10
Patent number
US04294760

Reaction notes

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