2-Methyl-6-nitro-1,3-benzoxazol-4-ol → 6-Amino-2-methyl-1,3-benzoxazol-4-ol

HRID 647220Notes

Reaction equation

HRID 647220 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([OH:14])[C:7]2[N:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=1)([O-])=O.[H][H]>C1COCC1.CO.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]([OH:14])[C:7]2[N:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=1

Participants

6

Reactant 2

HCID 204858692-Methyl-6-nitro-1,3-benzoxazol-4-olHCID 178418361HCID 178418361, compound

Product 1

HCID 204858816-Amino-2-methyl-1,3-benzoxazol-4-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-nitro-4-hydroxy-2-methylbenzoxazole (5.1 g, 0.026 mole) in THF (100 ml) and methanol (50 ml) were added about 0.5 g of 10 percent palladium on carbon. The mixture was placed on the Parr-shaker apparatus and hydrogenated two hours. At this time hydrogen uptake was complete (6.3 psi, 0.079 mole). The catalyst was removed and the solvents were removed under reduced pressure. The resulting off-white solid (4.1 g, 97.0 percent) was collected and dried. TLC showed the product to be pure. A ninhydrin test for amines was positive. A silver test for hydroxylamine was negative.

Workup

  1. customwas placed on the Parr-shaker apparatus and hydrogenated two hours
  2. customThe catalyst was removed
  3. customthe solvents were removed under reduced pressure
  4. customThe resulting off-white solid (4.1 g, 97.0 percent) was collected
  5. customdried

Sources & evidence

ORD record
ord-e664e72264094f2dbd26e2c171168d8e
Source dataset
uspto-grants-1983_10
Patent number
US04407930

Reaction notes

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