2-[2-(Pyridin-2-yl)ethyl]aniline → 6-[2-(2-Aminophenyl)ethyl]-N,N-diethylpyridine-3-carboxamide

HRID 1974091Notes

Reaction equation

HRID 1974091 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)=[N:7][CH:6]=1)[CH3:2].NC1C=CC=CC=1CCC1C=CC(C(N(CC)CC)=O)=CN=1.NC1C=CC=CC=1CCC1C=CC=CN=1>[Pd].C(O)C>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([N:3]([CH2:23][CH3:24])[CH2:1][CH3:2])=[O:22])=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 47154222-[2-(Pyridin-2-yl)ethyl]anilineHCID 68140930HCID 68140930, compound

Product 1

HCID 205599556-[2-(2-Aminophenyl)ethyl]-N,N-diethylpyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-(o-Aminophenethyl)-N,N-diethylnicotinamide N,N-diethyl-6-(o-nitrostyryl)nicotinamide (16.3 g., 0.05 mole) reduced in 150 ml. of ethanol employing 0.1 g. of 10% palladium on carbon catalyst according to the procedure described in Example 2 (a) for 2-(o-aminophenethyl)pyridine provides 6-(o-aminophenethyl)-N,N-diethylnicotinamide base. Addition of ethanolic hydrogen chloride to the nicotinamide base in ethanol provides 6-(o-aminophenethyl)-N,N-diethylnicotinamide dihydrochloride, m.p. 224°-226° C. (corr.).

Sources & evidence

ORD record
ord-10c897cac2ae4cb0bcc7e0b4160f6efd
Source dataset
uspto-grants-1976_12
Patent number
US04000143

Reaction notes

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