HCID 802799, compound → 2-(4-methylphenyl)-1,3-benzoxazol-5-amine

HRID 1896742Notes

Reaction equation

HRID 1896742 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH:19]=1)([O-])=O>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[C:15]1([CH3:18])[CH:14]=[CH:13][C:12]([C:10]2[O:11][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:19][C:8]=3[N:9]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 802799HCID 802799, compound

Product 1

HCID 7218792-(4-methylphenyl)-1,3-benzoxazol-5-amineYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22609514Ethyl acetate acetateSolvent

Procedure

To 5-nitro-2-p-tolylbenzo[d]oxazole (4.8 g, 18.90 mmol) in ethyl acetate/acetic acid (250 mL/1 mL) was added palladium on carbon (480 mg). The reaction vessel was purged three times with nitrogen, followed by hydrogen three times, and then left stirring under hydrogen for 16 h. The reaction vessel was finally purged three times with nitrogen, before filtration on a pad of Celite®, which was washed with ethyl acetate. The organic solution was washed with saturated aqueous Na2CO3, followed by brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 2.5 g (60%) of the title compound.

Workup

  1. customThe reaction vessel was purged three times with nitrogen
  2. waitleft
  3. customThe reaction vessel was finally purged three times with nitrogen
  4. filtrationbefore filtration on a pad of Celite®, which
  5. washwas washed with ethyl acetate
  6. washThe organic solution was washed with saturated aqueous Na2CO3
  7. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-c55ae85c07ac4428b4719d374e16e254
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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