Sodium Hydroxide → HCID 86711841, compound

HRID 623761Notes

Reaction equation

HRID 623761 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[CH:11][NH:10][C:9]=2[C:14]([O:16]CC)=[O:15])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[CH:11][NH:10][C:9]=2[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14462625HCID 14462625, compound

Product 1

HCID 86711841HCID 86711841, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl 3-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylate (11 g, 41.7 mmol) in methanol (140 mL,) and tetrahydrofuran (140 mL) was added sodium hydroxide (140 mL, 6M aqueous solution) and the reaction was stirred at 110° C. for 4 hrs. The reaction mixture was allowed to cool and the organics removed under vacuum. The resulting residue was slurried in water (200 mL) and acidified with acetic acid to pH4. The resulting precipitate was collected by filtration and washed with water to afford the title compound as a grey solid (9.8 g, 99% yield)

Workup

  1. temperatureto cool
  2. customthe organics removed under vacuum
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-ebabca755c5b45eea2744fb274658734
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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