Hydrochloric Acid → HCID 70102772, compound

HRID 365616Notes

Reaction equation

HRID 365616 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH:14]([C:20]3[C:25](F)=[CH:24][C:23](C#N)=[CH:22][C:21]=3F)C(OCC)=O)=[CH:10][C:9]=2[CH3:30])=[O:7])=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl.C[O:38][CH:39]([OH:41])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:20]3[CH:25]=[CH:24][C:23]([C:39]([OH:41])=[O:38])=[CH:22][CH:21]=3)=[CH:10][C:9]=2[CH3:30])=[O:7])=[CH:31][CH:32]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 30156371-MethoxyethanolHCID 23285969HCID 23285969, compound

Product 1

HCID 70102772HCID 70102772, compound

Procedure

To a slurry of ethyl 2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]-2-(2,6-difluoro-4-cyanophenyl)acetate (0.05 g, 0.11 mmol) [prepared as described in Example 9, Step (a)] in methoxyethanol (4 ml) was added an aqueous solution of lithium hydroxide monohydrate (0.02 g in 0.5 ml H2O), and the reaction mixture was heated at reflux under an argon atmosphere. After 24 hr, the reaction mixture was cooled to room temperature and poured into a mixture of ice/water (40 ml) containing 1N HCl (1 ml). The solid was filtered to give crude {4-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]benzoic acid (0.037 g) as a tan solid. Flash chromatography on a silica gel column (0.5% acetic acid-30% acetone:hexane), followed by recrystallization from methanol-acetone gave pure {4-[5-(4-chloro-benzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]benzoic acid (0.032 g, 70.2% yield) as a white solid, mp 245-246.8° C. ##STR47##

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux under an argon atmosphere
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-831f1c4abcc74166b7162ef03b292fc0
Source dataset
uspto-grants-2000_10
Patent number
US06127402

Reaction notes

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