Sodium Bicarbonate → HCID 12051830, compound

HRID 2228608Notes

Reaction equation

HRID 2228608 reaction equation
[OH:1][CH2:2][C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:5](COC)[C:4]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>Cl>[OH:1][CH2:2][C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[NH:5][C:4]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 12051829HCID 12051829, compound

Product 1

HCID 12051830HCID 12051830, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-Hydroxymethyl-1-methoxymethyl-4-methyl-2,5-di(4-pyridyl)-1H-pyrrole (150 mg, 0.49 mmol) was dissolved in 10% aqueous HCl solution (20 mL) and the mixture was stirred for 1 day at room temperature then heated at reflux temperature for 1 hour. After cooling, the mixture was neutralized with saturated aqueous sodium bicarbonate solution. Volatiles were removed by evaporation, and the residue was suspended in EtOH. After removal of insolubles by filtration, the filtrate was concentrated in vacto. The crude product was purified by flash chromatography eluting with CH2Cl2—EtOH (5:1), followed by recrystallization from EtOH to give the title compound (30 mg, 23% yield) as a solid.

Workup

  1. temperaturethen heated
  2. temperatureat reflux temperature for 1 hour
  3. temperatureAfter cooling
  4. customVolatiles were removed by evaporation
  5. customAfter removal of insolubles
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated in vacto
  8. customThe crude product was purified by flash chromatography
  9. washeluting with CH2Cl2—EtOH (5:1)
  10. customfollowed by recrystallization from EtOH

Sources & evidence

ORD record
ord-c1cca68c3a964f0b910cd4e620644b42
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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