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

HRID 566803Notes

Reaction equation

HRID 566803 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). After 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. 1H NMR: δ 7.34-7.30 (m, 2H), 7.10 (t, 2H, J=8.6 Hz), 6.97-6.95 (m, 2H), 6.29 (t, 1H, J=2.2 Hz), 3.60 (s, 2H). Anal. Calculated for C12H10NO2F•0.15 H2O: C, 64.95; H, 4.68; N, 6.31. Found: C, 65.03; H, 4.71; N, 6.25.

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-5c4c5adffa674e0fa062cd97b09ab265
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

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