2-tert-Butyl-7-nitro-6-phenyl-1,3-benzoxazole-4-carboxylic Acid → HCID 68584986, compound

HRID 17517Notes

Reaction equation

HRID 17517 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:8](=[C:10]([C:23]([OH:25])=[O:24])[CH:11]=[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]=2[N+:14]([O-])=O)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[C].[Pd]>[NH2:14][C:13]1[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]([C:23]([OH:25])=[O:24])=[C:8]2[C:7]=1[O:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:9]2

Participants

5

Reactant 2

HCID 685849732-tert-Butyl-7-nitro-6-phenyl-1,3-benzoxazole-4-carboxylic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 68584986HCID 68584986, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-tert-Butyl-7-nitro-6-phenyl-1,3-benzoxazole-4-carboxylic acid (I-223) (6.27 mmol) was dissolved in methanol (30 ml), then at room temperature, 10% palladium-carbon (430 mg) was added. The suspension was stirred at room temperature under atmospheric pressure of hydrogen for 16 hour. The catalyst was removed by filtration with washing with methanol, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:methanol=98:2) to obtain the entitled compound (1.274 g, 66% from I-222) as a pale brown powder.

Workup

  1. customThe catalyst was removed by filtration
  2. washwith washing with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:methanol=98:2)
  5. customto obtain the entitled compound (1.274 g, 66% from I-222) as a pale brown powder

Sources & evidence

ORD record
ord-c0e17637b46140c89d172dc850b67008
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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