Hydrochloric Acid → HCID 59463399, compound

HRID 1712967Notes

Reaction equation

HRID 1712967 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]1[N:12]([C:17]2[N:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=2)[C:13]([CH3:16])=[CH:14][CH:15]=1.Cl>[OH-].[Na+].CCO>[CH3:10][C:11]1[N:12]([C:17]2[N:22]=[CH:21][C:20]([C:23](=[O:25])/[CH:24]=[CH:4]/[C:3]3[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=3[OH:1])=[CH:19][CH:18]=2)[C:13]([CH3:16])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 534030171-[6-(2,5-Dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]ethan-1-one

Product 1

HCID 59463399HCID 59463399, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a vigorously stirred solution of 2-hydroxybenzaldehyde in 2.5N NaOH (2.2 mL) at 0° C. was added 1-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]ethanone (prepared by a method analogous to that described by Scott et al., Org. Proc. Res. And Dev., 8:587 (2004)) (0.58 g, 2.7 mmol) in EtOH (2 mL). The reaction mixture was allowed to stir and warm to rt whereupon an additional 1 mL of EtOH was added. The mixture turned a dark red color and was allowed to stir for 25 h. The reaction was neutralized by the addition of 1M HCl and the mixture was extracted with EtOAc. The organic solutions were combined, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give (2E)-1-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]-3-(2-hydroxyphenyl)prop-2-en-1-one as a yellow solid (0.31 g, 36%). LCMS: (FA) ES+ 319.2 (M+1).

Workup

  1. customprepared by a method analogous to
  2. additionwas added
  3. stirringto stir for 25 h
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1a8bbac8606045d089ff52ca56108b18
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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