Hydrochloric Acid → 2-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-acetic acid

HRID 382188Notes

Reaction equation

HRID 382188 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:6]=1.[Li+].[OH-].Cl>C1COCC1>[F:16][C:13]1[CH:14]=[CH:15][C:10]([N:7]2[CH:8]=[CH:9][C:5]([CH2:4][C:3]([OH:17])=[O:2])=[CH:6]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 543331132-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-acetic acid methyl ester

Product 1

HCID 183803942-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-acetic acid methyl ester (100 mg, 0.43 mmol) in THF (1 mL) at 0° C. was added dropwise 2N aqueous LiOH (0.5 mL). Afer warming to ambient temperature over 4 hours, the mixture was added dropwise to 0.5N aqueous HCl (10 mL). The resultant light brown solid was collected by filtration, washed with H2O, and dried in vacuo over P2O5 to yield 700 mg (74%) of analytically pure 2-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-acetic acid as a solid, mp 100-2° C.

Workup

  1. filtrationThe resultant light brown solid was collected by filtration
  2. washwashed with H2O
  3. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-763245d936c44c8a88a6055c1ea8a35e
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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