Propylamine → 2-(2-n-Propylaminoanilin-5-yl)benzoxazole

HRID 74220Notes

Reaction equation

HRID 74220 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.C(=O)([O-])[O-].[K+].[K+].[CH2:26]([NH2:29])[CH2:27][CH3:28].[H][H]>C(O)C.[C].[Pd].O>[CH2:26]([NH:29][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[NH2:17])[CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 7852PropylamineHCID 11430Potassium CarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674986522-(2-n-Propylaminoanilin-5-yl)benzoxazoleYield 49%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added potassium carbonate (176 mg, 1.28 mmol) and aqueous n-propylamine (82.4 mg, 1.39 mmol), and this was heated to reflux for 2.5 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (7 mL) of the crystals obtained was added 10% palladium-carbon (100 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 14 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (152 mg, 49% yield).

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 2.5 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a tetrahydrofuran solution (7 mL) of the crystals obtained
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-93f659a76f5f4b779baa27ce49f62da0
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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