Acetic Acid → 2-(2-Benzylaminoanilin-5-yl)benzoxazole

HRID 74180Notes

Reaction equation

HRID 74180 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][C:10]=1[N+:24]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C(O)C.C(=O)([O-])O.[Na+]>[Fe].C(Cl)(Cl)Cl>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][C:10]=1[NH2:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 674986602-(4-Benzylamino-3-nitrophenyl)benzoxazole

Product 1

HCID 674988042-(2-Benzylaminoanilin-5-yl)benzoxazoleYield 28%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6212ChloroformSolvent

Procedure

To a suspension of 2-(4-benzylamino-3-nitrophenyl)benzoxazole (see Working Example 17-1) (340 mg, 0.985 mmol) was added 10% aqueous acetic acid solution (5 mL), ethanol (8 mL), and iron powder (165 mg, 2.95 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution and chloroform were added, this was filtered through Celite and then extracted with chloroform. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give an oil that was purified by silica gel column chromatography to yield the title compound (87 mg, 28% yield) as brown crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux
  3. filtrationthis was filtered through Celite
  4. extractionextracted with chloroform
  5. customThe organic layer obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil that
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-125a3f86ab5e4b199ed5145fa749d225
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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