Ammonium formate → 1H-Imidazole-1-propanoic acid, 4-(4-aminophenyl)-, 1,1-dimethylethyl ester

HRID 2366886Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][N:13]([CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][N:13]([CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Palladium (10% w/w on carbon, 50% wet, 260 mg, 2.443 mmol) was added to a solution of 1,1-dimethylethyl 3-[4-(4-nitrophenyl)-1H-imidazol-1-yl]propanoate (for a preparation see Intermediate 97) (2.6 g, 8.19 mmol) and ammonium formate (1.29 g, 20.48 mmol) in ethanol (50 mL). The reaction mixture was refluxed for 4 h then was cooled to approximately 40° C. and filtered through celite whilst still warm. Most of the solvent was removed in vacuo from the filtrate to give 1,1-dimethylethyl 3-[4-(4-aminophenyl)-1H-imidazol-1-yl]propanoate (1.8 g, 6.26 mmol, 76%) as a yellow solid.

Workup

temperatureThe reaction mixture was refluxed for 4 h
filtrationfiltered through celite whilst
temperaturestill warm
customMost of the solvent was removed in vacuo from the filtrate

Sources & evidence

ORD record: ord-2a75f2d6d24e4dcb977351f1089ec7b6
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697725B2

Reaction notes

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