Triethylamine → [2,2-Dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-(3-nitroquinolin-4-yl)amine

HRID 2362544Notes

Reaction equation

HRID 2362544 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][C:16]([CH3:26])([CH2:19][C:20]1([CH3:25])[O:24][CH2:23][CH2:22][O:21]1)[CH2:17][NH2:18].C(N(CC)CC)C>ClCCl>[CH3:15][C:16]([CH3:26])([CH2:19][C:20]1([CH3:25])[O:21][CH2:22][CH2:23][O:24]1)[CH2:17][NH:18][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 57455404HCID 57455404, compound

Product 1

HCID 69506895[2,2-Dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-(3-nitroquinolin-4-yl)amineYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The general method described in Step 1 of Example 1 was used to react 4-chloro-3-nitroquinoline (21.8 g, 104 mmol), 2,2-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propylamine (19.8 g, 114 mmol) and triethylamine (15.2 g, 150 mmol) in dichloromethane for 75 hours to provide [2,2-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-(3-nitroquinolin-4-yl)amine (35.9 g) as a yellow solid that was used directly in the next step without further purification.

Sources & evidence

ORD record
ord-e51ad5af4f8b444a874d96bdec8495a0
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

Loading…