Dimethylformamide → HCID 86703355, compound

HRID 2173682Notes

Reaction equation

HRID 2173682 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=C(N)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.C([O-])([O-])=O.[K+].[K+].IC.[CH3:22][N:23]([CH:25]=O)[CH3:24]>>[CH3:1][O:2][C:3]1[CH:4]=[C:25]([N:23]([CH3:22])[CH3:24])[C:10]2[C:11]([CH:12]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 158689483-Methoxynaphthalen-1-amine

Product 1

HCID 86703355HCID 86703355, compound

Procedure

To a solution of 3-methoxy-1-aminonaphthalene (U.S. Pat. No. 7,018,431 B2, 0.13 g) in DMF (5 mL), K2CO3 (0.31 g) and iodomethane (0.09 mL) were added. After stirring for 24 hours, the reaction was partitioned between water (30 mL) and EtOAc (30 mL), the layers separated, and the organic layer washed with brine, dried (Na2SO4) and concentrated. The crude reaction purified over silica gel (gradient of EtOAc in heptane) to provide the title compound (0.14 g) as a clear oil: 1H NMR (DMSO-d6) δ 7.99 (d, 1H); 7.74 (d, 1H), 7.40 (ddd, 1H), 7.30 (ddd, 1H), 6.95 (d, 1H), 6.67 (d, 1H), 3.83 (s, 3H), 2.78 (s, 6H); MS expected 202 (C13H16NO, M+1), found 202.

Workup

  1. customthe reaction was partitioned between water (30 mL) and EtOAc (30 mL)
  2. customthe layers separated
  3. washthe organic layer washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude reaction
  7. custompurified over silica gel (gradient of EtOAc in heptane)

Sources & evidence

ORD record
ord-e12c3d6d79ca4e51add25ae9cdf40822
Source dataset
uspto-grants-2015_06
Patent number
US09056885B2

Reaction notes

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