Hydrochloric Acid → HCID 53392264, compound

HRID 1922485Notes

Reaction equation

HRID 1922485 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:7]1=O.[OH-].[Na+].Cl>O>[CH3:20][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 53392258HCID 53392258, compound

Product 1

HCID 53392264HCID 53392264, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

1-(3-(Dimethylamino)propyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (4.23 g, 15.25 mmol) was stirred in borane tetrahydrofuran complex, 1M (76 ml, 76 mmol) at 60° C. overnight. The reaction mixture was then cooled to 0° C. and quenched via addition of methanol. The resulting suspension was concentrated and then stirred in refluxing methanol (50 mL). To this solution was added sodium hydroxide (6.10 g, 153 mmol) as a solution in a minimal amount of water. The resulting mixture was refluxed at 90° C. After 1 h, no free product was observed, only product borane complex. The solution was then diluted with water and acidified with conc HCl and refluxed at 90° C. After 1 h, TLC analysis showed free product, and no borane complex. The mixture was then neutralized via addition of NaOH (3N) and extracted with dichloromethane (3×). 1H NMR (DMSO-d6) δ 7.87 (dd, J=9.3, 3 Hz, 1H), 7.77 (d, J=3 Hz, 1H), 6.68 (d, J=9.6 Hz, 1H), 3.43-3.38 (m, 4H), 2.74 (t, J=6 Hz, 2H), 2.23 (t, J=6.5 Hz, 2H), 2.13 (s, 6H), 1.85 (quint, J=6 Hz, 2H), 1.68 (quint, J=7 Hz, 2H). ESI-MS (m/z, %) 264 (MH+, 100).

Workup

  1. customat 60° C.
  2. customovernight
  3. customquenched via addition of methanol
  4. concentrationThe resulting suspension was concentrated
  5. temperaturein refluxing methanol (50 mL)
  6. temperatureThe resulting mixture was refluxed at 90° C
  7. temperaturerefluxed at 90° C
  8. waitAfter 1 h
  9. extractionextracted with dichloromethane (3×)

Sources & evidence

ORD record
ord-2e24eb846f084232aa0e3924d5762eda
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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