Ammonium Chloride → (4-Benzyloxy-benzyl)-quinolin-6-yl-amine

HRID 2080260Notes

Reaction equation

HRID 2080260 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:33]=[CH:32][C:18]([C:19]([NH:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CC=CC=1OCC1C=CC(CNC(C2C(N)=NC(N)=CN=2)=O)=CC=1.[Cl-].[NH4+]>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][NH:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)=[CH:32][CH:33]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23130518HCID 23130518, compoundHCID 58875320HCID 58875320, compound

Product 1

HCID 58875328(4-Benzyloxy-benzyl)-quinolin-6-yl-amineYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (58 mg, 1.54 mmol) in tetrahydrofuran (10 mL) was added a solution of 4-benzyloxy-N-quinolin-6-yl-benzamide described in Preparation Example Z+-3 (218 mg, 0.615 mmol) in tetrahydrofuran (1 mL), and the solution was stirred under reflux for 7 hours. The reaction solution was allowed to room temperature, an aqueous solution of saturated ammonium chloride was added, the solution was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane: ethyl acetate), and the title compound (147 mg, 70%) was obtained as a yellow solid.

Workup

  1. temperatureunder reflux for 7 hours
  2. customwas allowed to room temperature
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by NH silica gel column chromatography (hexane: ethyl acetate)

Sources & evidence

ORD record
ord-d85b9663ac114467940b276b0cbad6e6
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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