Acetic Acid → 2-(2-(4-Methoxycarbonylphenylmethyl)aminoanilin-5-yl)benzoxazole

HRID 74298

Reaction equation

HRID 74298 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:20][C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:15][C:14]=2[N+:28]([O-])=O)=[CH:7][CH:6]=1)=[O:4].C(O)(=O)C.CO.C(=O)([O-])O.[Na+]>[Fe].C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:20][C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:15][C:14]=2[NH2:28])=[CH:9][CH:10]=1)=[O:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 674984512-(2-(4-Methoxycarbonylphenylmethyl)aminonitrobenzen-5-yl)benzoxazole

Product 1

HCID 674985672-(2-(4-Methoxycarbonylphenylmethyl)aminoanilin-5-yl)benzoxazoleYield 18.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6212ChloroformSolvent

Procedure

To 2-(2-(4-methoxycarbonylphenylmethyl)aminonitrobenzen-5-yl)benzoxazole (see Working Example 113-2) (367 mg, 0.910 mmol) was added iron powder (102 mg, 1.82 mmol), 10% aqueous acetic acid (5 mL) and methanol (7 mL), and this was heated to reflux for 16 hours. After the reaction solution was cooled, saturated aqueous sodium hydrogen carbonate solution and chloroform were added, this was filtered through Celite, and the filtrate obtained was extracted. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (61.8 mg, 18% yield).

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 16 hours
  3. temperatureAfter the reaction solution was cooled
  4. filtrationthis was filtered through Celite
  5. customthe filtrate obtained
  6. extractionwas extracted
  7. customAfter the organic layer obtained
  8. dry with materialwas dried over anhydrous sodium sulfate, it
  9. filtrationwas filtered
  10. concentrationconcentrated
  11. customThe residue obtained
  12. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e4345ba1d1c04e26b9671a58bffa3f66
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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