HCID 13094268, compound → HCID 13094269, compound

HRID 1153736Notes

Reaction equation

HRID 1153736 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][C:11]#[N:12])=[N:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 13094268HCID 13094268, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13094269HCID 13094269, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-2-(3-cyanopropyl)-3-methylpyridine (23.0 g) was reduced with lithium aluminium hydride (12.47 g) in a mixture of tetrahydrofuran (750 ml) and diethylether (750 ml) over 3 hours, to give 5-amino-2-(4-aminobutyl)-3-methylpyridine (20.8 g) as an amber oil. N.M.R. (CDCl3): assignment, δ (p.p.m.) multiplicity; --CH2CH2CH2NH2, 1.3-1.9, m; 3--CH3, 2.22, s; CH2 (CH2)2CH2NH2, 2.6-2.8, m; 5--NH2, ca 3.5, broad resonance; 4-pyridyl proton, 6.77, d; 6-pyridyl proton, 7.88, d.

Sources & evidence

ORD record
ord-3ed63ef868814ed69114e3ec5e9a3efb
Source dataset
uspto-grants-1984_12
Patent number
US04486434

Reaction notes

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