Hydrochloric Acid → 1-methyl-5-phenyl-1H-pyrrole-2-carboxylic acid

HRID 2301886Notes

Reaction equation

HRID 2301886 reaction equation
[OH-].[Li+].[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:6]=[C:5]1[C:15]([O:17]C)=[O:16].CO.Cl>O.C1COCC1>[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:6]=[C:5]1[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 22350789methyl 1-methyl-5-phenyl-1H-pyrrole-2-carboxylate

Product 1

HCID 223507001-methyl-5-phenyl-1H-pyrrole-2-carboxylic acidYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide (1.39 g, 33.2 mmol) is added to a solution of the product from Step 152b (1.43 g, 6.64 mmol) in 96 mL of a 1.25:1:1 H2O:MeOH:THF solvent mixture. The reaction is stirred at 50° C. for 2 h. Aqueous HCl (1N, 50 mL) is added and the resultant precipitate is collected by filtration, washed with water, and dried to give 0.851 g of 1-methyl-5-phenyl-1H-pyrrole-2-carboxylic acid as a tan solid (64% yield). MS for C12H11NO2 (ESI) (M−H)+ m/z 200.1.

Workup

  1. filtrationthe resultant precipitate is collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-d0dec2eb29c6481cbaf1340e86fee7d5
Source dataset
uspto-grants-2002_12
Patent number
US06500840B2

Reaction notes

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