Sodium Bicarbonate → HCID 18470722, compound

HRID 2228605Notes

Reaction equation

HRID 2228605 reaction equation
[C:1]([C:4]1[C:8]([CH2:9][O:10]C)=[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[NH:6][C:5]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+]>Cl>[C:1]([C:4]1[C:8]([CH2:9][OH:10])=[C:7]([C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)[NH:6][C:5]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18470743HCID 18470743, compound

Product 1

HCID 18470722HCID 18470722, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

3-Acetyl-4-methoxymethyl-2,5-di(4-pyridyl)-1H-pyrrole (0.36 g, 1.17 mmol) was dissolved in 10% aqueous HCl solution (14 mL). The mixture was heated at 70° C. for 15 hours. After cooling, the mixture was neutralized with saturated aqueous sodium bicarbonate solution. Insolubles were filtered off, and the filtrate was extracted with ethyl acetate-EtOH (5:1, 200 mL×2). The combined organic layers were washed with brine (50 mL), dried over MgSO4, and concentrated ill vaciio. The crude product was recrystallized from ethyl acetate to provide the title product (150 mg, 44% yield) as a solid.

Workup

  1. temperatureAfter cooling
  2. filtrationInsolubles were filtered off
  3. extractionthe filtrate was extracted with ethyl acetate-EtOH (5:1, 200 mL×2)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated ill vaciio
  7. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8fc820da9c5f4742a2b9135cfee1f953
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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