6,7-Dimethoxy-2-tetralone → 4-Benzyloxy-N-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-naphthalenyl)aniline

HRID 1110449Notes

Reaction equation

HRID 1110449 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][C:8](=O)[CH2:7][CH2:6]2.Cl.[CH2:17]([O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH3-]C#N.[Na+]>CO>[CH2:17]([O:24][C:25]1[CH:26]=[CH:27][C:28]([NH:29][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)=[CH:30][CH:31]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6098446,7-Dimethoxy-2-tetraloneHCID 27238314-Benzyloxyaniline hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 150782284-Benzyloxy-N-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-naphthalenyl)anilineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 500 mg (2.42 mmol, Aldrich) of 6,7-dimethoxy-2-tetralone and 570 mg (2.42 mmol, Aldrich) of 4-benzyloxyaniline hydrochloride in 20 ml of MeOH was stirred over 3A molecular sieves at 25° C., then 76 mg (1.21 mmol, Aldrich) of NaBH3CN were added. This mixture was stirred for 3.5 hours, filtered and then saturated NaHCO3 was added to the filtrate. This solution was extracted with EtOAc twice, the organic layers were combined, dried (MgSO4) and concentrated in vacuo. Purification via flash chromatography (silica gel, 8, 1:5 then 1:3 EtOAc/petroleum ether) afforded mg (90%) of title compound as a pale pink solid:m.p. 85°-88° C.

Workup

  1. filtrationfiltered
  2. additionsaturated NaHCO3 was added to the filtrate
  3. extractionThis solution was extracted with EtOAc twice
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification via flash chromatography (silica gel, 8, 1:5

Sources & evidence

ORD record
ord-fe4348ef4bf24fe7a5bcf64a67eda743
Source dataset
uspto-grants-1990_12
Patent number
US04975461

Reaction notes

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