Water → HCID 66620230, compound

HRID 1364049Notes

Reaction equation

HRID 1364049 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].[Br:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](Cl)=[C:26]([N+:31]([O-:33])=[O:32])[CH:27]=[N:28]2)=[CH:23][CH:22]=1.O>CN(C=O)C>[Br:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[C:26]([N+:31]([O-:33])=[O:32])[CH:27]=[N:28]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 219843617-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 66620230HCID 66620230, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (8.9 mL, 64 mmol) and tert-butyl N-(3-aminopropyl)carbamate (30.95 g, 177.6 mmol) were added to a solution of 7-bromo-4-chloro-3-nitroquinoline (42.55 g, 148.0 mmol, U.S. patent application publication no. US 2004/0147543, Example 1, Parts A through D) in DMF (500 mL), and the reaction was stirred for four days at ambient temperature. The reaction mixture was poured into water (2 L), and a precipitate formed. The precipitate was isolated by filtration and dried in a vacuum oven overnight at 65° C. to provide 56.4 g of tert-butyl 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propylcarbamate.

Workup

  1. customa precipitate formed
  2. customThe precipitate was isolated by filtration
  3. customdried in a vacuum oven overnight at 65° C.

Sources & evidence

ORD record
ord-b00fe75c96674e9aba3fc88c3a9aa015
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

Loading…