Acetone → HCID 86691918, compound

HRID 717752Notes

Reaction equation

HRID 717752 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([N:12]=O)[CH2:7][CH:6]([C:14]1[CH:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=1)[CH2:5]2.[Cl-].[NH4+].O.[CH3:24][C:25]([CH3:27])=O>[Zn]>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([N:12]=[C:25]([CH3:27])[CH3:24])[CH2:7][CH:6]([C:14]1[CH:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=1)[CH2:5]2

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 25517Ammonium ChlorideHCID 86691919HCID 86691919, compound

Product 1

HCID 86691918HCID 86691918, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
15 °C

Procedure

To a stirred solution of 6-methyl-3-(6-methylpyridin-3-yl)-1-nitroso-1,2,3,4-tetrahydroquinoline (0.28 g, 0.00104 mol) in acetone (15 mL) was added saturated ammonium chloride solution (0.8 mL) and water (0.8 mL) at RT. The resulting brown colored reaction mixture was cooled to 15° C. Zinc dust (0.954 g, 0.0146 mol) was added portionwise at the same temperature. After the addition, the reaction mixture was stirred for 1 h at RT. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure and the residue extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and the solvent removed under reduced pressure to obtain product as a brown colored oil (0.28 g, 91% yield).

Workup

  1. additionAfter the addition
  2. customAfter completion of reaction (monitored by TLC), solvent
  3. customwas removed under reduced pressure
  4. extractionthe residue extracted with EtOAc
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1514af0d81084e82bf04a4585ab96f95
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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