Ammonium formate → N-[methoxy]-N-[methyl]3-cyclopentylamino-4-aminobenzamide

HRID 250726Notes

Reaction equation

[CH3:1][O:2][N:3]([CH3:21])[C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[C:7]([NH:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=1.C([O-])=O.[NH4+]>C(O)C>[CH3:1][O:2][N:3]([CH3:21])[C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Combine N-[methoxy]-N-[methyl]3-cyclopentylamino-4-nitrobenzamide (2.0 g, 6.82 mmol), ammonium formate (2.1 g, 34.1 mmol), and 0.36 g (3.41 mmol) Pd(C) in ethanol (25 mL). Heat the mixture to 60° C. and stir for two hours. Cool to room temperature and filter through a pad of celite. Concentrate the filtrate under reduced pressure to provide the desired compound (1.79 g).

Workup

temperatureCool to room temperature
filtrationfilter through a pad of celite
concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record: ord-964367c669c44984bf3e7ba5a4e0ce27
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863310B2

Reaction notes

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