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

HRID 2040447Notes

Reaction equation

HRID 2040447 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 (4:1 Hexane: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 (4:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-24b79f6d86f74d04b30b0d82204296f1
Source dataset
uspto-grants-2013_11
Patent number
US08580840B2

Reaction notes

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