Ammonium Chloride → HCID 22935748, compound

HRID 1352506Notes

Reaction equation

HRID 1352506 reaction equation
[Br-].[C:2]([N:5]([CH:23]1[CH2:25][CH2:24]1)[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N+:9]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=1)(=[O:4])[CH3:3].[CH3:26][Mg]Cl.[Cl-].[NH4+]>O1CCCC1.CO>[CH2:16]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([N:5]([CH:23]2[CH2:25][CH2:24]2)[C:2](=[O:4])[CH3:3])=[CH:7][CH:8]1[CH3:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 22935706HCID 22935706, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 22935748HCID 22935748, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-(acetyl-cyclopropyl-amino)-1-benzyl-quinolinium bromide (9.6 g) in tetrahydrofuran (200 ml), under nitrogen and under cooling at 0° C., a solution of methyl magnesium chloride 1 Mol/l (12 ml) was added during 15 minutes. After 2 hours, a solution of ammonium chloride in methanol (100 ml) was added. The solvent was removed under reduce pressure and then washed with dichloromethane and water. The organic layer was separated and the solvent was removed under reduce pressure. The crude compound was purified by flash chromatography on silicagel with an eluent of dichloromethane/methanol (98/2) to give the N-(1-benzyl-2-methyl-1,2-dihydro-quinolin-4-yl)-N-cyclopropyl-acetamide (7.9 g, 98.6% yield).

Workup

  1. customThe solvent was removed
  2. washwashed with dichloromethane and water
  3. customThe organic layer was separated
  4. customthe solvent was removed
  5. customThe crude compound was purified by flash chromatography on silicagel with an eluent of dichloromethane/methanol (98/2)

Sources & evidence

ORD record
ord-19c2f1eb3e11478983ee1f4a1e79343d
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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