p-Toluenesulfonic acid → (6,7-Dimethoxyquinolin-4-yl)methyl(4-nitrophenyl)amine

HRID 573433Notes

Reaction equation

HRID 573433 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:16][NH:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.COCC(O)C>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[N:17]([CH3:16])[C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7483N-Methyl-4-nitroanilineHCID 79001-Methoxy-2-propanolHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 89581532(6,7-Dimethoxyquinolin-4-yl)methyl(4-nitrophenyl)amineYield 40%

Procedure

4-Chloro-6,7-dimethoxyquinoline (0.50 g, 2.24 mmol), N-methyl(4-nitrophenyl)amine; (0.564 g, 3.35 mmol) and p-toluenesulfonic acid (0.192 g, 1.12 mmol) in 1-methoxy-2-propanol (6.56 mL, 67.1 mmol) were heated to 120° C. for 8 h. The reaction was cooled to rt, triturated with ether and filtered to yield (6,7-dimethoxyquinolin-4-yl)methyl(4-nitrophenyl)amine (0.40 g, 40%). LCMS m/z=340 (M+1); 1H NMR (CDCl3) δ: 8.80 (d, 1H, J=4.8 Hz), 8.10 (d, 2H, J=9.4 Hz), 7.5 (brs, 1H), 7.16 (d, 1H, J=4.8), 6.84 (s, 1H), 6.64 (d, 2H, J=9.4 Hz), 4.05 (s, 3H), 3.81 (s, 3H), 3.52 (s, 3H).

Workup

  1. customtriturated with ether
  2. filtrationfiltered

Sources & evidence

ORD record
ord-36a6b54a31164203994e847c80331f1d
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

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