Methyl 5-methyl-2-(4-nitrophenyl)oxazole-4-carboxylate → Methyl 2-(4-aminophenyl)-5-methyl-1,3-oxazole-4-carboxylate

HRID 43577Notes

Reaction equation

HRID 43577 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:16]([O:18][CH3:19])=[O:17]>[Pd].CO>[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[O:6][C:2]([CH3:1])=[C:3]([C:16]([O:18][CH3:19])=[O:17])[N:4]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 67548650Methyl 5-methyl-2-(4-nitrophenyl)oxazole-4-carboxylate

Product 1

HCID 68405990Methyl 2-(4-aminophenyl)-5-methyl-1,3-oxazole-4-carboxylateYield 66.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The same operation as in Example (95b) was performed using methyl 5-methyl-2-(4-nitrophenyl)-1,3-oxazole-4-carboxylate obtained in Example (97c) (0.75 g, 2.86 mmol), 10% Pd/C (0.3 g) and methanol (10 mL). Purification by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 1/2, 1/4) gave 0.44 g of the title compound as a colorless solid (66%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 1/2, 1/4)

Sources & evidence

ORD record
ord-6759ee8b96bf434dbd4615ca55a464dd
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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