Triethylamine → Ethyl 5-[(3,5-dinitropyridin-2-yl)amino]pentanoate

HRID 1967468Notes

Reaction equation

HRID 1967468 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)CC)C>O1CCOCC1>[N+:8]([C:7]1[C:2]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:3][CH:4]=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 757382-Chloro-3,5-dinitropyridineHCID 11469139ETHYL 5-AMINOVALERATE

Product 1

HCID 86643267Ethyl 5-[(3,5-dinitropyridin-2-yl)amino]pentanoateYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A procedure similar to that of the method described in step C.1 is carried out, starting from 1.2 g (5.9 mmol) of 2-chloro-3,5-dinitropyridine, 1.03 g (7.07 mmol) of ethyl 5-aminovalerate and 0.9 g (8.84 mmol) of triethylamine in 20 ml of dioxane. This gives 1.4 g of expected product.

Sources & evidence

ORD record
ord-1b295fce7bcc4287bbf5ca5e306e87e1
Source dataset
uspto-grants-2013_04
Patent number
US08420817B2

Reaction notes

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