Hydrochloric Acid → HCID 89618001, compound

HRID 589310Notes

Reaction equation

HRID 589310 reaction equation
[N:1]1([CH2:6][C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[CH2:12][CH2:11][CH2:10]2)=O)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.[OH-].[Na+]>C1COCC1>[N:1]1([CH2:6][CH2:7][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89618124HCID 89618124, compound

Product 1

HCID 89618001HCID 89618001, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 100-ml round-bottomed, three-necked flask fitted with a condenser and a thermometer, under an inert (nitrogen) atmosphere, 8.6 g (30 mmol) of 2-(1H-imidazol-1-yl)-1-(7-nitro-3,4-dihydroquinolin-1-(2H)-yl)ethanone are dissolved in 10 ml of dry THF. The solution was stirred at 0° C. and 150 ml (5 eq) of a 1.0M solution of BH3 in THF were added. The reaction medium was left to return to ambient temperature and was then stirred overnight. The reaction mixture was carefully acidified (drop by drop) with 1N HCl (considerable foaming and release of gas), before being brought to reflux for 0.5 h. The mixture was then cooled to ambient temperature and neutralized with 4.0N sodium hydroxide. The medium is extracted several times with ethyl acetate. The organic phases were combined, and dried over MgSO4. After filtration, the solvent was removed by evaporation. The residue was purified by chromatography on a column of silica (dichloromethane/methanol). After evaporation of the solvents, crystallization was initiated with diethyl ether so as to give the expected product: 1-(2-(1H-imidazol-1-yl)ethyl)-7-nitro-1,2,3,4-tetrahydroquinoline in the form of an orange solid (Mp 120-121° C.).

Workup

  1. customIn a 100-ml round-bottomed, three-necked flask fitted with a condenser
  2. waitThe reaction medium was left
  3. customto return to ambient temperature
  4. stirringwas then stirred overnight
  5. temperatureto reflux for 0.5 h
  6. extractionThe medium is extracted several times with ethyl acetate
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtration
  9. customthe solvent was removed by evaporation
  10. customThe residue was purified by chromatography on a column of silica (dichloromethane/methanol)
  11. customAfter evaporation of the solvents, crystallization

Sources & evidence

ORD record
ord-b9855b015cfd4697b5f9e277aaffcd46
Source dataset
uspto-grants-2016_01
Patent number
US09233060B2

Reaction notes

Loading…