Ethanol → [3-Chloro-1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

HRID 2071675Notes

Reaction equation

HRID 2071675 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])[N:4]([CH3:16])[C:3]=1[CH2:17][C:18]([O:20]C)=[O:19].C(O)C>[OH-].[Na+]>[Cl:1][C:2]1[CH:6]=[C:5]([C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[O:8])[N:4]([CH3:16])[C:3]=1[CH2:17][C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 702EthanolHCID 21411867Methyl 3-chloro-1-methyl-5-(p-toluoyl)pyrrole-2-acetate

Product 1

HCID 21411833[3-Chloro-1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 3.3 g. of methyl 3-chloro-1-methyl-5-(p- toluoyl)pyrrole-2-acetate (0.0108 mole) from Example II in 12 ml. of IN sodium hydroxide and 5 ml. of ethanol is refluxed for 30 min. The ethanol is evaporated from the yellow solution, and the latter is poured into dilute HCl. The precipitate is collected, air dried, and recrystallized from 2-propanol to give 3-chloro-1-methyl-5-(p-toluoyl) pyrrole-2-acetic acid as a white solid; m.p. 163°-164° C (dec.)

Workup

  1. additionA suspension of 3.3 g
  2. customThe ethanol is evaporated from the yellow solution
  3. additionthe latter is poured into dilute HCl
  4. customThe precipitate is collected
  5. customair dried
  6. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-9658fd9d33024a9db9d1ff56579b138b
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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