tert-butyl N-(4-aminobutyl)carbamate → tert-Butyl (4-((3-nitroquinolin-4-yl)amino)butyl)carbamate

HRID 1837558Notes

Reaction equation

HRID 1837558 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].Cl.Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27]>>[N+:26]([C:17]1[CH:18]=[N:19][C:20]2[C:25]([C:16]=1[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[CH:24][CH:23]=[CH:22][CH:21]=2)([O-:28])=[O:27]

Participants

3

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 224789924-Chloro-3-nitroquinoline hydrochloride

Product 1

HCID 22381766tert-Butyl (4-((3-nitroquinolin-4-yl)amino)butyl)carbamateYield 99,886.898%

Procedure

Using the general method of Example 1 Part A, tert-butyl N-(4-aminobutyl)carbamate (254 g, 1.35 mol) was reacted with 4chloro-3-nitroquinoline hydrochloride (331 g, 1.35 mmol) to provide 486 g of tert-butyl N-(4-[(3-nitroquinolin-4yl)amino]butyl)carbamate as yellow solid. Analysis: Calculated for C18H24N4O4: %C, 59.99; %H, 6.71; %N, 15.55; Found: %C, 59.68; %H, 6.59; %N, 15.74.

Sources & evidence

ORD record
ord-5cc432ecc70844c58c845387eb3ba2dc
Source dataset
uspto-grants-2004_08
Patent number
US06784188B2

Reaction notes

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