Ethanol → 4-Amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide

HRID 32286

Reaction equation

HRID 32286 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:9])=[C:6]([O:20][CH3:21])[CH:5]=1)([O-])=O.C(O)C>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]([CH2:14][CH3:15])[CH2:16][CH3:17])=[O:9])=[C:6]([O:20][CH3:21])[CH:5]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 4088914-nitro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide

Product 1

HCID 773744-Amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamideYield 106.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.7 g (19.3 mmol) of 4-nitro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide is dissolved in 120 ml of tetrahydrofuran:ethanol=1:1, mixed with 2 g of palladium on carbon (10%×50% water) and hydrogenated for 1 hour at room temperature and normal pressure. After being drawn off on diatomaceous earth and after concentration by evaporation, 5.45 g of 4-amino-N-(2-diethylamino-ethyl)-2-methoxy-benzamide is obtained.

Workup

  1. concentrationafter concentration
  2. customby evaporation

Sources & evidence

ORD record
ord-a4a84b761f37465986edb7e193759a3c
Source dataset
uspto-grants-2008_09
Patent number
US07427390B2

Linked notes

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