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

HRID 43597Notes

Reaction equation

HRID 43597 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[O:13][CH:14]=[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].C(O)C>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:12]2[O:13][CH:14]=[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 67549178Methyl 2-(3-methoxy-4-nitrophenyl)-1,3-oxazole-4-carboxylate

Product 1

HCID 67549244Methyl 2-(4-amino-3-methoxyphenyl)-1,3-oxazole-4-carboxylateYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The same operation as in Example (95b) was performed using methyl 2-(3-methoxy-4-nitrophenyl)-1,3-oxazole-4-carboxylate obtained in Example (102c) (1.46 g, 5.25 mmol), 10% Pd/C (0.3 g) and ethanol (20 mL). The resulting solid was washed with dichloromethane/hexane to obtain 0.88 g of the title compound as a colorless solid (67%).

Workup

  1. washThe resulting solid was washed with dichloromethane/hexane

Sources & evidence

ORD record
ord-3cf346220a3d4943972faef280c01636
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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