Sodium Dithionite → [3-Fluoro-4-methyl-2-(1-naphthalenyloxy)phenyl]amine

HRID 1875046Notes

Reaction equation

HRID 1875046 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[F:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]([N+:17]([O-])=O)[C:11]=1[O:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>O.C1COCC1>[F:9][C:10]1[C:11]([O:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)=[C:12]([NH2:17])[CH:13]=[CH:14][C:15]=1[CH3:16]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 684854931-[(2-Fluoro-3-methyl-6-nitrophenyl)oxy]naphthalene

Product 1

HCID 68487227[3-Fluoro-4-methyl-2-(1-naphthalenyloxy)phenyl]amineYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium hydrosulfite (25.8 g, 125 mmol) in water (120 mL) was added dropwise to a solution of 1-[(2-fluoro-3-methyl-6-nitrophenyl)oxy]naphthalene (6.2 g, 20.86 mmol) in THF (60 mL) at room temperature. The mixture was stirred at room temperature for 2 hrs. The reaction mixture was extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (hexane:ethyl acetate) to give the title compound (3.34 g, 60%) as a light tan oil. 1H NMR (400 MHz, chloroform-d) δ ppm 8.44-8.52 (m, 1H), 7.80-7.90 (m, 1H), 7.45-7.61 (m, 3H), 7.19-7.32 (m, 1H), 6.86 (t, 1H), 6.64 (d, 1H), 6.53 (dd, 1H), 3.59 (br. s., 2H), 2.19 (s, 3H). ES MS m/z 268 (M+1).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×50 mL)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-aa0971ac842741c9b178eebc7f069ff9
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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