2-(4-n-Butylamino-3-nitrophenyl)benzoxazole → 2-(2-n-Butylaminoanilin-5-yl)benzoxazole

HRID 74245Notes

Reaction equation

HRID 74245 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:8][C:7]=1[N+:21]([O-])=O)[CH2:2][CH2:3][CH3:4].[H][H]>[C].[Pd].O1CCCC1>[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:8][C:7]=1[NH2:21])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 674984732-(4-n-Butylamino-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674988512-(2-n-Butylaminoanilin-5-yl)benzoxazoleYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (5 mL) of 2-(4-n-butylamino-3-nitrophenyl)benzoxazole (see Working Example 74-1) (353 mg, 1.13 mmol) was added 10% palladium-carbon (50 mg), a hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 15 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 (305 mg, 96% yield).

Workup

  1. filtrationthis was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue obtained
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-af1524baa09746e5a53c1f3415b04052
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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