Acetone → HCID 86691927, compound

HRID 717770Notes

Reaction equation

HRID 717770 reaction equation
[N:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH2:4]1)=O.[Cl-].[NH4+].O.[CH3:22][C:23]([CH3:25])=O>[Zn]>[CH3:22][C:23](=[N:1][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH2:4]1)[CH3:25]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 25517Ammonium ChlorideHCID 86691926HCID 86691926, compound

Product 1

HCID 86691927HCID 86691927, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
0 °C

Procedure

To a solution of 1-nitroso-3-(pyridin-4-yl)-1,2,3,4-tetrahydroquinoline (0.41 g, 0.00171 mol) in acetone (22 mL) was added saturated ammonium chloride solution (1.4 mL) and water (1.4 mL) at RT. The resulting brown colored reaction mixture was cooled to 0° C., and then zinc dust (0.669 g, 0.0102 mol) was added portionwise at 0° C. After addition, the reaction mixture was warmed to RT and stirred for 1 h. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure and the residue extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate, solvent was removed under reduced pressure to obtain product as a brown colored oil (0.3 g).

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was warmed to RT
  3. customAfter completion of reaction (monitored by TLC), solvent
  4. customwas removed under reduced pressure
  5. extractionthe residue extracted with EtOAc (3×100 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate, solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-512c722b1b504678bb6bd361224f3a0d
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

Loading…