(4-Methoxyphenyl)hydrazine → 8-Methoxy-6,11-dihydrothiochromeno[4,3-b]indole

HRID 1391654Notes

Reaction equation

HRID 1391654 reaction equation
CO[C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[CH2:8][CH2:9][S:10]2)=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]N)=[CH:18][CH:17]=1>CCO>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:19](=[CH:20][CH:21]=1)[NH:22][C:7]1[C:6]3[CH:5]=[CH:4][CH:3]=[CH:12][C:11]=3[S:10][CH2:9][C:8]2=1

Participants

4

Reactant 2

HCID 77023(4-Methoxyphenyl)hydrazineHCID 849527HCID 849527, compound

Product 1

HCID 2891388-Methoxy-6,11-dihydrothiochromeno[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-methoxy-thiochroman-4-one (700 mg, 4.27 mmol) was stirred with (4-methoxy-phenyl)-hydrazine (818 mg, 4.70 mmol, 1.1 eq.) in EtOH (40 mL, 0.1 M) and refluxed for 2 hours. EtOH was then removed from the mixture and EtOAc and saturated NaHCO3 aqueous solution were added. The organic layer was separated, dried over K2CO3 and concentrated. The residue was purified with flash column chromatography (4:1Hexane:EtOAc) to yield the title product as a brown solid.

Workup

  1. temperaturerefluxed for 2 hours
  2. customEtOH was then removed from the mixture and EtOAc and saturated NaHCO3 aqueous solution
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried over K2CO3
  6. concentrationconcentrated
  7. customThe residue was purified with flash column chromatography (4:1Hexane:EtOAc)

Sources & evidence

ORD record
ord-1fe2175ba2df4ea690f5f920d7a853c2
Source dataset
uspto-grants-2008_03
Patent number
US07338973B2

Reaction notes

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