Acetone → HCID 86691935, compound

HRID 717792Notes

Reaction equation

HRID 717792 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([N:18]=O)[CH2:9]2)=[CH:4][CH:3]=1.[Cl-].[NH4+].O.[CH3:23][C:24]([CH3:26])=O>[Zn]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([N:18]=[C:24]([CH3:26])[CH3:23])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 25517Ammonium ChlorideHCID 86691934HCID 86691934, compound

Product 1

HCID 86691935HCID 86691935, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-fluorophenyl)-1-nitroso-1,2,3,4-tetrahydroquinoline (0.27 g, 0.00105 mol) in acetone (15 mL) was added saturated ammonium chloride solution (1.5 mL) and water (1.5 mL) at RT. The resulting brown colored reaction mixture was cooled to 0° C., and zinc dust (0.411 g, 0.00632 mol) was added portionwise at 0° C. After addition, the reaction mixture was warmed to RT and stirred for 2 h. After completion of reaction (monitored by TLC), the solvent was removed under reduced pressure and the residue extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and solvent was removed under reduced pressure to obtain product as a brown colored oil (0.28 g).

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was warmed to RT
  3. customAfter completion of reaction (monitored by TLC)
  4. customthe solvent was 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 and solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-931f3177a5d446b6ad2dbf03798c6b28
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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