Ethyl 2-(4-isopropoxy-3-nitrophenyl)-4-methyl-5-thiazolecarboxylate → Ethyl 2-[3-amino-4-(propan-2-yloxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate

HRID 1051294Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[C:14]([N+:22]([O-])=O)[CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C.[Pd]>[NH2:22][C:14]1[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][C:15]=1[O:18][CH:19]([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

A reaction mixture solution prepared by suspending 1.38 g of ethyl 4-methyl-2-[3-nitro-4-(propan-2-yloxy)phenyl]-1,3-thiazole-5-carboxylate in 15 mL of ethanol and adding 100 mg of palladium/carbon (10 wt %) to the suspension was heated under stirring at 50° C. for 14 hours under a hydrogen atmosphere. The reaction mixture solution was celite-filtered and the filtrate was concentrated under reduced pressure to obtain 1.26 g of ethyl 2-[3-amino-4-(propan-2-yloxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate.

Workup

customA reaction mixture solution prepared
temperaturewas heated
filtrationThe reaction mixture solution was celite-filtered
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-51667163ef4f47a79339b953f0f88d91
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388174B2

Reaction notes

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