2-(4-Neopentylamino-3-nitrophenyl)benzoxazole → 2-(2-Neopentylaminoanilin-5-yl)benzoxazole

HRID 74257Notes

Reaction equation

HRID 74257 reaction equation
[CH2:1]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][C:8]=1[N+:22]([O-])=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[H][H]>[C].[Pd].O1CCCC1>[CH2:1]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][C:8]=1[NH2:22])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 674990142-(4-Neopentylamino-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674978662-(2-Neopentylaminoanilin-5-yl)benzoxazoleYield 89.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (5 mL) of 2-(4-neopentylamino-3-nitrophenyl)benzoxazole (see Working Example 81-1) (242 mg, 0.744 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 (196 mg, 89% 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-11f03d1e0fb8423a8aaa20d19de03e28
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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