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

HRID 1108642Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26]>C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

3.59 g (19.08 mmol) of N-(tert-butoxycarbonyl)-1,4-diaminobutane was dissolved in 70 ml of triethylamine and 3.79 g (18.17 mmol) of 4-chloro-3-nitroquinoline was added thereto. The resulting mixture was heated at 70° C. and stirred for 4 hours. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in chloroform, washed with water, and dried (MgSO4). The solvent was distilled off under reduced pressure. The resulting residue was triturated with diethel ether and collected by filtration to obtain 5.77 g (16.01 mmol) of 4-[4-(tert-butoxycarbonylamino)butylamino]-3-nitroquinoline shown below as a yellow solid.

Workup

concentrationAfter the reaction mixture was concentrated under reduced pressure
dissolutionthe residue was dissolved in chloroform
washwashed with water
dry with materialdried (MgSO4)
distillationThe solvent was distilled off under reduced pressure
customThe resulting residue was triturated with diethel ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-86a25cd833ed4682b816e61fcec38681
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069149

Reaction notes

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