Hydrochloric Acid → HCID 89618108, compound

HRID 589312Notes

Reaction equation

HRID 589312 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=3)[CH2:14][CH2:13][CH2:12]2)=O)[CH2:4][CH2:3]1.Cl.[OH-].[Na+]>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=3)[CH2:14][CH2:13][CH2:12]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67412355HCID 67412355, compound

Product 1

HCID 89618108HCID 89618108, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 6 g (18 mmol) of 2-(4-methylpiperazin-1-yl)-1-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone are dissolved in 20 ml of anhydrous THF. With stirring, at 0° C., a solution of 100 ml of 1.0M BH3 in THF (5.5 eq) is added. The temperature was allowed to return to ambient temperature and stirring was carried out for 24 h, before acidifying (drop by drop) with 1N HCl (considerable foaming and release of gas), and the medium was then brought to reflux for 0.5 h. After a return to ambient temperature, a 4.0N aqueous solution of NaOH was added. The medium was extracted several times with ethyl acetate. The combined organic phases were dried over Na2SO4, and then filtered. After removal of the solvent, a residue was obtained, which was purified on a silica column (dichloromethane-methanol). 1-(2-(4-Methylpiperazin-1-yl)ethyl)-7-nitro-1,2,3,4-tetrahydroquinoline was thus obtained in the form of an orange powder (Mp 58-60° C.).

Workup

  1. customto return to ambient temperature
  2. stirringstirring
  3. temperatureto reflux for 0.5 h
  4. extractionThe medium was extracted several times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customAfter removal of the solvent
  8. customa residue was obtained
  9. customwhich was purified on a silica column (dichloromethane-methanol)

Sources & evidence

ORD record
ord-f3b152b7347a4bf69d777ea593f17ec3
Source dataset
uspto-grants-2016_01
Patent number
US09233060B2

Reaction notes

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