Hydrochloric Acid → HCID 67279753, compound

HRID 1524317Notes

Reaction equation

HRID 1524317 reaction equation
[CH2:1]([N:8]([CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][N+:13]([O-:16])=[CH:12][C:11]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([N:8]([CH2:19][CH2:20][OH:21])[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][N+:13]([O-:16])=[CH:12][C:11]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67279782HCID 67279782, compound

Product 1

HCID 67279753HCID 67279753, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the compound (1.20 g) obtained in step 2 in MeOH (5 mL) was added 6N hydrochloric acid (5 mL), and the mixture was stirred at 60° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a mixture of ethyl acetate and THF. The solution was neutralized with aqueous sodium hydroxide solution, and the resultant product was extracted three times with a mixture of ethyl acetate and THF, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 66% ethyl acetate/hexane→5% ammonia/ethyl acetate) to give N-benzyl-3-fluoro-N-(2-hydroxyethyl)isonicotinamide 1-oxide (0.63 g, 73%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and THF
  3. extractionthe resultant product was extracted three times
  4. additionwith a mixture of ethyl acetate and THF
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (solvent gradient; 66% ethyl acetate/hexane→5% ammonia/ethyl acetate)

Sources & evidence

ORD record
ord-ffd96f986336418b9be86bcefc0c6949
Source dataset
uspto-grants-2015_07
Patent number
US09079907B2

Reaction notes

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