Ethyl 2-(3-nitro-4-phenoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate → Ethyl 2-(3-amino-4-phenoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 1051306Notes

Reaction equation

HRID 1051306 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:17]2[S:18][C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]([CH3:22])[N:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:17]2[S:18][C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]([CH3:22])[N:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 118555045Ethyl 2-(3-nitro-4-phenoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 118555046Ethyl 2-(3-amino-4-phenoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylateYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A reaction mixture solution prepared by suspending 1.14 g of ethyl 2-(3-nitro-4-phenoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate in 15 mL of ethanol and adding 300 mg of palladium/carbon (10 wt %) was stirred at room temperature for 14 hours under a hydrogen atmosphere. The reaction mixture solution was celite-filtered and the filtrate was concentrated under reduced pressure to obtain 1.05 g of ethyl 2-(3-amino-4-phenoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate.

Workup

  1. customA reaction mixture solution prepared
  2. filtrationThe reaction mixture solution was celite-filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-de9f89073de141068724fc1a1034ad92
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

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