Sodium Hydroxide → HCID 11591337, compound

HRID 456846Notes

Reaction equation

HRID 456846 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[CH:32][CH:31]=2)[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO.O>[C:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:38][CH:39]=2)[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 18439047HCID 18439047, compound

Product 1

HCID 11591337HCID 11591337, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-({[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)benzoate (235 mg, 0.461 mmol), prepared in the previous step, and 1 N NaOH (692 μL, 0.692 mmol) in 30 mL of THF plus 30 mL of methanol plus 5 mL of water was refluxed under nitrogen for 7 h. The reaction was filtered, cooled to room temperature, acidified by the addition of 2.5 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (225 mg, 99%) as a white solid, mp 309–310° C. Elemental Analysis for C34H25NO3.0.05 C4H8O.0.19 H2O Calc'd: C, 81.73; H, 5.17; N, 2.79. Found: C, 81.94; H, 5.02; N, 2.65.

Workup

  1. temperaturewas refluxed under nitrogen for 7 h
  2. filtrationThe reaction was filtered
  3. additionacidified by the addition of 2.5 mL of 1 N HCl
  4. concentrationconcentrated under reduced pressure
  5. customto remove the THF and methanol
  6. filtrationThe solid present was collected by filtration
  7. washrinsed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-306b11e3c58b49099bbfcf2a0da3500b
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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