Hydrochloric Acid → HCID 68839395, compound

HRID 2105769Notes

Reaction equation

HRID 2105769 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[O:18][CH3:19])[N:7]([CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:6]=1[CH3:27])=[O:4].[OH-].[Na+].Cl>O1CCOCC1.O>[CH:21]1([CH2:20][N:7]2[C:8]([C:10]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=3[O:18][CH3:19])=[CH:9][C:5]([C:3]([OH:4])=[O:2])=[C:6]2[CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68838780HCID 68838780, compound

Product 1

HCID 68839395HCID 68839395, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2.3 g of 1-cyclohexylmethyl-5-(2,5-dimethoxy-phenyl)-2-methyl-1H-pyrrole-3-carboxylic acid methyl ester in dioxane (50 ml) and water (50 ml) was added 18.8 ml of a 1N solution of sodium hydroxide. The reaction mixture was heated at reflux for 16 hours. After such time the reaction mixture was allowed to cool down to room temperature before being neutralized with 18.8 ml of a 1N solution of hydrochloride acid. Dioxane was distilled off and the precipitate was then filtered and washed with water to give 2.1 g of the title compound; MS (ISP) 356.3 (M−H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 hours
  3. distillationDioxane was distilled off
  4. filtrationthe precipitate was then filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-6b643e51b47546fd8f1fb39a99607140
Source dataset
uspto-grants-2009_08
Patent number
US07579369B2

Reaction notes

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