Hydrochloric Acid → HCID 20271455, compound

HRID 326083Notes

Reaction equation

HRID 326083 reaction equation
N[C:2]1[C:3]([CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.N([O-])=O.[Na+].[ClH:18]>[Cu]>[Cl:18][C:2]1[C:3]([CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20271442HCID 20271442, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20271455HCID 20271455, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

Reaction of 3-amino-2-(4-aminobutyl)-5-methylpyridine from Example 1(d) (0.5 g) with sodium nitrite, cuprous chloride, copper bronze and hydrochloric acid under conditions analogous to those of Example 1(e) gave 3-chloro-2-(4-aminobutyl)-5-methylpyridine (0.43 g) as an oil. N.M.R. (CDCl3) assignment δ(p.p.m.), multiplicity; NH2, 1.56, s; CH2 (CH2)2CH2NH2, 1.4-1.9, m; 5--CH3, 2.29, s; --CH2NH2, 2.74; m; --CH2 (CH2)3NH2, 2.91, m; 4H+6H pyridyl protons, 7.45+8.24, m×2;

Sources & evidence

ORD record
ord-65dcaca441494b03bd45753701d2ef5a
Source dataset
uspto-grants-1984_04
Patent number
US04444772

Reaction notes

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