Ammonia → Ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

HRID 1950057Notes

Reaction equation

HRID 1950057 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH:23]2[CH2:32][CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([O:33][CH3:34])[CH:29]=3)[CH2:24]2)=[C:17]([NH:19][C:20](=O)[CH3:21])[CH:18]=1.N>O1CCCC1>[CH2:20]([NH:19][C:17]1[CH:18]=[C:13]([O:12][CH3:11])[CH:14]=[CH:15][C:16]=1[CH:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:33][CH3:34])[CH:29]=2)[CH2:24]1)[CH3:21]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 66626357N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamide

Product 1

HCID 23087318Ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amineYield 57.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine (1.0 g) in pyridine (5 ml) was added acetic anhydride (5 ml), and the solution was stirred for 10 minutes at room temperature. An ice water was added thereto, the solution was stirred, was neutralized with a saturated aqueous solution of sodium bicarbonate, and the resulting solid was filtered and purified by silica gel column chromatography (hexane-ethyl acetate system) to provide N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamide (1.1 g). To a suspension of lithium aluminum hydride (400 mg) in tetrahydrofuran (20 ml) was added aluminum chloride (1.4 g) on an ice bath under a nitrogen atmosphere, the solution was stirred for 15 minutes at room temperature, then N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamide (1.1 g) was added thereto followed by stirring for 1 hour at room temperature. Tetrahydrofuran and aqueous ammonia were sequentially added thereto, the resulting suspension was filtered through celite pad, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (604 mg).

Workup

  1. stirringby stirring for 1 hour at room temperature
  2. filtrationthe resulting suspension was filtered through celite pad
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-32cd6344cea24055aca85e49d9ae96ca
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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