Hydrochloric Acid → Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate

HRID 1888972Notes

Reaction equation

HRID 1888972 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:19])=[C:8](C(OC(C)(C)C)=O)[NH:9][C:10]=1[CH3:11])=[O:5])[CH3:2].Cl>C(O)(C)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:19])=[CH:8][NH:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 43476602-Tert-butyl 4-ethyl 3,5-dimethyl-1h-pyrrole-2,4-dicarboxylate

Product 1

HCID 137481Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
47.5 °C

Procedure

Into a 10-L four necked round-bottomed flask equipped with a mechanical stirrer, a thermometer pocket, gas bubbler and an air condenser, were charged 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-tertiary butyl ester 4-ethyl ester (II) (1.5 Kg; 5.6 mole), isopropyl alcohol 4.5 L and stirred while Conc. HCl (2.2 L) was charged with the aid of addition funnel at 25-30° C. After addition, the temperature of the reaction mixture was raised to 45-50° C. and maintained at this temperature until the gas evolution completely ceases. The reaction was monitored by TLC and the solution cooled to 25-30° C. and quenched in a carboy containing ice water under stirring. The product was isolated by filtration and dried at 50° C.

Workup

  1. additionwas charged with the aid of addition funnel at 25-30° C
  2. additionAfter addition
  3. temperaturemaintained at this temperature until the gas evolution
  4. temperaturethe solution cooled to 25-30° C.
  5. customquenched in a carboy
  6. additioncontaining ice water
  7. customThe product was isolated by filtration
  8. customdried at 50° C.

Sources & evidence

ORD record
ord-247f4d768cce49e7b5501697d88dd720
Source dataset
uspto-grants-2013_08
Patent number
US08501962B2

Reaction notes

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