Methyl iodide → 5-Methoxynaphthalen-2-amine

HRID 2173680Notes

Reaction equation

HRID 2173680 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[CH:7][CH:6]=[CH:5]2.[H-].[Na+].I[CH3:16]>CN(C=O)C>[CH3:16][O:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([NH2:1])=[CH:3]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 902956-Aminonaphthol

Product 1

HCID 129927625-Methoxynaphthalen-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-aminonaphth-1-ol (1.0 g) in DMF (50 mL), NaH (60% in mineral oil, 0.17 g) was added, and the reaction was stirred for 1 hour. Iodomethane (0.39 mL) was added, and the reaction was stirred for another 1 hour. The reaction was then partitioned between NaHCO3 (aq., 150 mL) and EtOAc (100 mL), the layers separated, and the organic layer washed with brine, dried (Na2SO4) and concentrated. The crude reaction was purified over silica gel (gradient of EtOAc in heptane) to provide the title compound (0.8 g) as an orange oil:: 1H NMR (DMSO-d6) δ 7.81 (d, 1H); 7.16 (dd, 1H), 7.04 (d, 1H), 6.85 (dd, 1H), 6.75 (d, 1H), 6.53 (dd, 1H), 5.32 (s, 2H), 3.86 (s, 3H).

Workup

  1. stirringthe reaction was stirred for another 1 hour
  2. customThe reaction was then partitioned between NaHCO3 (aq., 150 mL) and EtOAc (100 mL)
  3. customthe layers separated
  4. washthe organic layer washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude reaction
  8. customwas purified over silica gel (gradient of EtOAc in heptane)

Sources & evidence

ORD record
ord-3167aba5f8de4b85bf9421dc69095ca4
Source dataset
uspto-grants-2015_06
Patent number
US09056885B2

Reaction notes

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