Sodium Hydroxide → HCID 12897078, compound

HRID 1981016Notes

Reaction equation

HRID 1981016 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][C:4]([C:15]([O:17]C)=[O:16])=[CH:3]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[C:6]([C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][C:4]([C:15]([OH:17])=[O:16])=[CH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12897077HCID 12897077, compound

Product 1

HCID 12897078HCID 12897078, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The entire batch of methyl 1-methyl-5-benzoylpyrrole-3-carboxylate from Example 84 was combined with 200 ml. of ethanol and 100 ml. of 1N sodium hydroxide and refluxed for 2 hours. The ethanol was boiled away, the aqueous residue was cooled to room temperature, extracted with 25 ml. of ether and acidified with conc. hydrochloric acid to yield crystalline product (4 g., m.p. 210°-212° C.). A portion (1.5 g.) was recrystallized from acetone to yield purified 1-methyl-5-benzoylpyrrole-3-carboxylic acid (925 mg., m.p. 215°-216.5° C., m/e 229).

Workup

  1. extractionextracted with 25 ml
  2. customto yield crystalline product (4 g., m.p. 210°-212° C.)
  3. customA portion (1.5 g.) was recrystallized from acetone
  4. customto yield
  5. custompurified 1-methyl-5-benzoylpyrrole-3-carboxylic acid (925 mg., m.p. 215°-216.5° C., m/e 229)

Sources & evidence

ORD record
ord-47256f59d19f45218c8cbe26dc4efe3c
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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