2-(1-Methyl-1H-pyrrol-2-yl)-5-nitro-1,3-benzoxazole → 2-(1-Methyl-1H-pyrrol-2-yl)-1,3-benzoxazol-5-amine

HRID 1287664Notes

Reaction equation

HRID 1287664 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[O:8][C:9]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:10]=2[N:11]=1>CCO.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:9]2[O:8][C:7]([C:3]3[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=3)=[N:11][C:10]=2[CH:12]=1

Participants

4

Reactant 1

HCID 127819152-(1-Methyl-1H-pyrrol-2-yl)-5-nitro-1,3-benzoxazole

Product 1

HCID 215056582-(1-Methyl-1H-pyrrol-2-yl)-1,3-benzoxazol-5-amineYield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.5 g of 2-(1-methyl-2-pyrrolyl)-5-nitrobenzoxazole (0.006 mole) and 0.15 g of 10% Pd/C are suspended in 100 ml of 95% EtOH and hydrogenated at 50 psi over a period of 2.5 hr. The catalyst is removed and the EtOH evaporated under vacuum yielding a brown solid. Crystallization from methanol yields 1.15 g of tan crystals, mp 183°-185° (89%).

Workup

  1. customThe catalyst is removed
  2. customthe EtOH evaporated under vacuum
  3. customyielding a brown solid
  4. customCrystallization from methanol

Sources & evidence

ORD record
ord-64bcba1ee8cc47a599266016d636c5ea
Source dataset
uspto-grants-1976_10
Patent number
US03985755

Reaction notes

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