Sodium Hydroxide → 3-Carboxy-1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetic acid

HRID 1282359Notes

Reaction equation

HRID 1282359 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])=[C:5]([CH3:16])[C:4]([C:17]([O:19]CC)=[O:18])=[C:3]1[CH2:22][C:23]([O:25]CC)=[O:24].[OH-].[Na+]>>[C:17]([C:4]1[C:5]([CH3:16])=[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])[N:2]([CH3:1])[C:3]=1[CH2:22][C:23]([OH:25])=[O:24])([OH:19])=[O:18]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 18424258Ethyl 1,4-dimethyl-3-ethoxycarbonyl-5-(p-toluoyl)-pyrrole-2-acetate

Product 1

HCID 184243523-Carboxy-1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetic acid

Procedure

A suspension of 54 g. (0.145 mole) of ethyl 1,4-dimethyl-3-ethoxycarbonyl-5-(p-toluoyl)-pyrrole-2-acetate in 500 g. of 25% sodium hydroxide is heated at just below reflux for 3 hours. The yellow suspension is then poured into ice-hydrochloric acid, and the precipitated solid is collected, air dried and recrystallized from acetone-water to give 3-carboxy-1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetic acid as a white solid, m.p. 229-230° C. Anal. Calcd. for C17H17NO5: C, 64.75; H, 5.43; N, 4.44%. Found: C, 64.86; H, 5.53; N, 4.47%.

Workup

  1. additionA suspension of 54 g
  2. temperaturebelow reflux for 3 hours
  3. customthe precipitated solid is collected
  4. customair dried
  5. customrecrystallized from acetone-water

Sources & evidence

ORD record
ord-7b195628b93d4c498324bd900fdbe9b2
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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