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

HRID 1521631Notes

Reaction equation

HRID 1521631 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(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

4

Reactant 2

HCID 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

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 6-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione (109-4; 3.0 g, 0.011 mol) in n-butanol (25 mL) was added acetic hydrazide (4.81 g, 0.065 mol) and then followed by the addition of molecular sieves. Reaction mass was heated to 120° C. for 16 h. The reaction mixture was concentrated and directly purified by silica gel column chromatography to obtain title compound. MS (M+1): 284.2.

Workup

  1. additionfollowed by the addition of molecular sieves
  2. customReaction mass
  3. concentrationThe reaction mixture was concentrated
  4. customdirectly purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8fac951b220944dc8a63c6884d37f91d
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

Loading…