N,N-diethyl-3-nitro-4-[(2-phenylethyl)amino]benzamide → 3-amino-N,N-diethyl-4-[(2-phenylethyl)amino]benzamide

HRID 1796460Notes

Reaction equation

HRID 1796460 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([N+:20]([O-])=O)[CH:6]=1)[CH3:2]>CCOC(C)=O.[Pd]>[NH2:20][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[NH:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:4]([N:3]([CH2:1][CH3:2])[CH2:24][CH3:25])=[O:23]

Participants

4

Reactant 1

HCID 22181379N,N-diethyl-3-nitro-4-[(2-phenylethyl)amino]benzamide

Product 1

HCID 221813213-amino-N,N-diethyl-4-[(2-phenylethyl)amino]benzamideYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure 2C: A mixture of N,N-diethyl-3-nitro-4[(2-phenylethyl)amino]benzamide (0.170 g, 0.498 mmol) and 10% Pd/C in EtOAc (10 mL) was hydrogenated at 40 psi. Usual work-up provided the title compound (0.156 g) which was used without further purification. MS (ESI) (M+H)+=312.

Sources & evidence

ORD record
ord-e0036e05688e4fbabc204e962e980402
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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