p-Toluenesulfonic acid → HCID 53264706, compound

HRID 2272733Notes

Reaction equation

HRID 2272733 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.[N+:16]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)([O-:18])=[O:17].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[NH:23][C:22]1[CH:24]=[CH:25][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74754-NitroanilineHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 53264706HCID 53264706, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 79001-Methoxy-2-propanolSolvent

Procedure

4-Chloro-6,7-dimethoxyquinoline (0.40 g, 1.79 mmol, p-nitroaniline (0.414 g, 2.68 mmol) and p-toluenesulfonic acid (0.154 g, 0.894 mmol) in 1-methoxy-2-propanol (5 mL) were heated to 120° C. for 8 h. The mixture was cooled to rt, triturated with ether and filtered to yield (6,7-dimethoxyquinolin-4-yl)-(4-nitrophenyl)amine (0.43 g, 73%). LCMS m/z=326 (M+1); 1H NMR (DMSO) δ: 14.37 (s, 1H), 10.72 (s, 1H), 8.54 (d, 1H, J=6.80 Hz), 8.39 (d, 2H, J=9.08 Hz), 8.05 (s, 1H), 7.74 (d, 2H, J=9.09 Hz), 7.47 (d, 1H, 8.13 Hz), 7.43 (s, 1H), 7.19 (d, 1H, J=6.85), 7.10 (d, 1H, J=7.84), 4.02 (d, 7H, J=5.48), 2.28, (s, 1H).

Workup

  1. customtriturated with ether
  2. filtrationfiltered

Sources & evidence

ORD record
ord-2cee5d0040b547f5b6e41623aa520e7b
Source dataset
uspto-grants-2015_09
Patent number
US09120778B2

Reaction notes

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