4-Methoxyphenylhydrazine hydrochloride → HCID 10778313, compound

HRID 2040485Notes

Reaction equation

HRID 2040485 reaction equation
[S:1]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=O)[CH2:3][CH2:2]1.Cl.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21]N)=[CH:17][CH:16]=1>CCO>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:19][CH:20]=1)[NH:21][C:4]1[C:5]3[CH:10]=[CH:9][CH:8]=[N:7][C:6]=3[S:1][CH2:2][C:3]2=1

Participants

4

Reactant 2

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 120278442,3-Dihydro-4H-thiopyrano[2,3-b]pyridin-4-one

Product 1

HCID 10778313HCID 10778313, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,3-dihydro-thiopyrano[2,3-b]pyridin-4-one (2.24 g, 13.6 mmoL) and 4-methoxy-phenylhydrazine HCl salt (2.60 g, 14.9 mmoL) in EtOH (10 mL) was refluxed for 5 hours. The reaction mixture was cooled and filtrated through a pad of Celite to remove any solids in the mixture. The solvent was removed in vacuo. The remaining residue was partitioned between EtOAc and saturated NaHCO3. The aqueous phase was extracted two times with EtOAc. The organic layer of each extraction was washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the oil) was, then purified by column chromatography (silica gel, hexanes: EtOAc1:1 as eluent) to yield the title compound as a pale solid.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltrated through a pad of Celite
  4. customto remove any solids in the mixture
  5. customThe solvent was removed in vacuo
  6. customThe remaining residue was partitioned between EtOAc and saturated NaHCO3
  7. extractionThe aqueous phase was extracted two times with EtOAc
  8. extractionThe organic layer of each extraction
  9. washwas washed with water, brine
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto yield a brown oil
  14. custompurified by column chromatography (silica gel, hexanes: EtOAc1:1 as eluent)

Sources & evidence

ORD record
ord-8f50be51e8364121a3e9ad3c63361dd3
Source dataset
uspto-grants-2013_11
Patent number
US08580840B2

Reaction notes

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