Water → 7-Bromo-9-fluoro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 1521673Notes

Reaction equation

HRID 1521673 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[NH:8][C:7](=S)[CH2:6][CH2:5]2.[C:14]([NH:17][NH2:18])(=O)[CH3:15].C(OCC)(=O)C.O>C(O)CCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]1[C:14]([CH3:15])=[N:17][N:18]=[C:7]1[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14039AcetohydrazideHCID 891560716-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione

Product 1

HCID 709780527-Bromo-9-fluoro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 6-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione (157-4, 1.71 g, 6.57 mmol) and acetohydrazide (0.58 g, 7.89 mmol) in n-butanol (7 mL) was refluxed for 18 h under inert atmosphere. After cooling down to ambient temperature, ethyl acetate (10 mL) and water (10 mL) were added. Then the organic phase was separated, and the water phase was extracted with ethyl acetate (5×10 mL). The combined organic phases were washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The crude compound was purified by flash chromatography on silica gel to obtain title compound (white solid). 1H NMR (DMSO-D6, 500 MHz) 6=7.79 (dd, J=2.0 Hz, JHF=11.0 Hz, 1H), 7.63 (s, 1H), 2.95 (br s, 4H), 2.46 (d, JHF=8.5 Hz, 3H).

Workup

  1. temperaturewas refluxed for 18 h under inert atmosphere
  2. customThen the organic phase was separated
  3. extractionthe water phase was extracted with ethyl acetate (5×10 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude compound was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-06a158e339df4f6eb434d5baca19c572
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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