Hydrochloric Acid → 1H-Pyrrole-2-acetic acid, 1-methyl-, ethyl ester

HRID 1855720Notes

Reaction equation

HRID 1855720 reaction equation
Cl.[CH3:2][N:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])#N>CCOCC>[CH3:2][N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73041-MethylpyrroleHCID 69336Ethyl cyanoformate

Product 1

HCID 974691H-Pyrrole-2-acetic acid, 1-methyl-, ethyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 28 ml solution of ethereal hydrogen chloride (0.049 mole of HCl) is added dropwise over a 3 hr period to a solution of 2.1 g of N-methylpyrrole and 2.9 g of ethyl cyanoformate in 3 ml ether. The ether supernatant is decanted off, and the precipitate taken up in 11 mls of dry pyridine and the mixture transferred to a pressure bottle. Hydrogen sulfide (13 g) is added to the mixture at -78° C., the bottle sealed, and the mixture is stirred at ambient temperature overnight (about 16 hours). Gas chromatographic analysis with internal standards shows 57% yield of ethyl N-methylpyrrole-2-acetate.

Workup

  1. customThe ether supernatant is decanted off
  2. additionHydrogen sulfide (13 g) is added to the mixture at -78° C.
  3. customthe bottle sealed

Sources & evidence

ORD record
ord-d423666a2e7341d98059aa08f58ab014
Source dataset
uspto-grants-1980_08
Patent number
US04216150

Reaction notes

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