Methyl 2-(3-methoxy-4-nitrophenyl)-5-methyl-1,3-oxazole-4-carboxylate → Methyl 2-(4-amino-3-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylate

HRID 43612Notes

Reaction equation

HRID 43612 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[O:13][C:14]([CH3:21])=[C:15]([C:17]([O:19][CH3:20])=[O:18])[N:16]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>[Pd].CO>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:12]2[O:13][C:14]([CH3:21])=[C:15]([C:17]([O:19][CH3:20])=[O:18])[N:16]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 68405823Methyl 2-(3-methoxy-4-nitrophenyl)-5-methyl-1,3-oxazole-4-carboxylate

Product 1

HCID 67549647Methyl 2-(4-amino-3-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylateYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The same operation as in Example (95b) was performed using methyl 2-(3-methoxy-4-nitrophenyl)-5-methyl-1,3-oxazole-4-carboxylate obtained in Example (105c) (0.75 g, 2.57 mmol), 10% Pd/C (0.2 g) and methanol (20 mL), to obtain 0.68 g of the title compound as a yellow solid (100%).

Sources & evidence

ORD record
ord-7011432aa0084d8c816096b69f86cb54
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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