2-Bromopropane → HCID 20207250, compound

HRID 542809Notes

Reaction equation

HRID 542809 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]([C:13]2[NH:17][N:16]=[N:15][N:14]=2)=[CH:3]1.[CH:18](Br)([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH:18]([N:16]1[NH:15][N:14]=[C:13]([C:4]2[C:5](=[O:12])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:2]([CH3:1])[CH:3]=2)[NH:17]1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 63582-Bromopropane3×HCID 11430Potassium CarbonateHCID 178480143HCID 178480143, compound

Product 1

HCID 20207250HCID 20207250, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1-methyl-3-(1H-tetrazol-5-yl)-4-quinolone (0.74 g), isopropyl bromide (0.31 ml), anhydrous potassium carbonate (0.45 g) and butanone (30 ml) was boiled under reflux for 16 hours. More isopropyl bromide (0.5 ml) was added and boiling under reflux was continued for 7 hours. More isopropyl bromide (0.5 ml) was added and boiling under reflux was continued for a further 24 hours. The mixture was evaporated to dryness and the residue treated with water (30 ml). The solid product was collected by filtration and partially purified by high pressure liquid chromatography over silica gel using dichloromethane:methanol 95:5 as the eluent. The solid product was recrystallised from ethyl acetate:diethyl ether 3:2 to give the novel compound 3-(2-isopropyl-1H-tetrazol-5-yl)-1-methyl-4-quinolone, m.p. 134°-137°.

Workup

  1. temperatureunder reflux for 16 hours
  2. temperatureunder reflux
  3. temperatureunder reflux
  4. waitwas continued for a further 24 hours
  5. customThe mixture was evaporated to dryness
  6. additionthe residue treated with water (30 ml)
  7. filtrationThe solid product was collected by filtration
  8. custompartially purified by high pressure liquid chromatography over silica gel
  9. customThe solid product was recrystallised from ethyl acetate:diethyl ether 3:2

Sources & evidence

ORD record
ord-b5df9efa34494354abb636151129255a
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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