Methanol → 5-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

HRID 74186

Reaction equation

HRID 74186 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13](C2CCOCC2)=[C:14]([N+:16]([O-])=O)[CH:15]=1.[CH3:25][OH:26]>C1COCC1.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:3][CH:4]2[CH2:5][CH2:6][O:26][CH2:25][CH2:9]2)=[C:14]([CH:15]=1)[NH2:16]

Participants

5

Reactant 2

HCID 887MethanolHCID 674981085-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)nitrobenzene

Product 1

HCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoanilineYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)nitrobenzene (see Working Example 20-1) (1.00 g, 0.76 mol) was dissolved in a solvent mixture of THF (50 mL) and methanol (50 mL), and Pd/C (5%, wet, 0.5 g) was added to carry out a hydrogenation reaction. After being stirred overnight at room temperature, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to yield the title compound (812 mg, 89.1%) as a gray solid.

Workup

  1. additionwas added
  2. customa hydrogenation reaction
  3. customthe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-db448fdc435e4d0a9b8ec2680e8c8fa4
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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