2-(4-Isoproylamino-3-nitrophenyl)benzoxazole → 2-(2-Isopropylaminoanilin-5-yl)benzoxazole

HRID 74254Notes

Reaction equation

HRID 74254 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][C:6]=1[N+:20]([O-])=O)([CH3:3])[CH3:2].[H][H]>[C].[Pd].O1CCCC1>[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][C:6]=1[NH2:20])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 674980622-(4-Isoproylamino-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674987282-(2-Isopropylaminoanilin-5-yl)benzoxazoleYield 91.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (5 mL) of 2-(4-isopropylamino-3-nitrophenyl)benzoxazole (see Working Example 80-1) (224 mg, 0.753 mmol) was added 10% palladium-carbon (40 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 (184 mg, 91% 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-c8e3833fc24a433e9f5c15781aa1edf9
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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