Ammonium formate → Ethyl 2-(4-aminophenyl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 43566Notes

Reaction equation

HRID 43566 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C([O-])=O.[NH4+]>[Pd].CO>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:4]2[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 3824379Ethyl 4-methyl-2-(4-nitrophenyl)thiazole-5-carboxylate

Product 1

HCID 58326687Ethyl 2-(4-aminophenyl)-4-methyl-1,3-thiazole-5-carboxylateYield 75.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The same operation as in Example (90d) was performed using ethyl 4-methyl-2-(4-nitrophenyl)-1,3-thiazole-5-carboxylate obtained in Example (94a) (0.40 g, 1.36 mmol), 10% Pd/C (wet, 1.2 g), ammonium formate (0.52 g, 8.22 mmol) and methanol (10 mL), to obtain 0.27 g of the crude title compound as a light yellow solid (75%).

Sources & evidence

ORD record
ord-6edf86cdcf8f476a8aaa9138c1536017
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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