4,7-Dichloroquinoline → 4-[(7-Chloro-4-quinolinyl)amino]benzoic acid methyl ester hydrochloride

HRID 1586970Notes

Reaction equation

HRID 1586970 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1>CO>[ClH:1].[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([NH:13][C:2]2[C:11]3[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 68664,7-DichloroquinolineHCID 12082Methyl 4-aminobenzoate

Product 1

HCID 678596174-[(7-Chloro-4-quinolinyl)amino]benzoic acid methyl ester hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4,7-Dichloroquinoline (19.8 g, 100 mmol) and methyl 4-aminobenzoate (15.1 g, 100 mmol) are stirred in 150 mL of methanol in a 500 mL Erlenmeyer flask and heated on a hot plate. After~15 minutes, a yellow solid precipitates out of solution. Another 100 mL of methanol are added and the large chunks of material are broken up. After another 15 minutes of heating, the flask is allowed to cool for 5 minutes and the product is filtered and washed with ether. Air drying in the funnel overnight affords 26.01 g (74.5 mmol, 75% yield) of compound as a pale-yellow solid: 1H NMR (Me2SO-d6, 300 MHz) δ8.74 (d, J=9.3 Hz, 1H), 8.63 (d, J=6.9 Hz, 1H), 8.11 (d, J=8.7 Hz, 2H), 8.09 (d, J=2.1 Hz, 1H), 7.9 (d of d, 1 H), 7.62 (d, J=8.4 Hz, 2H), 7.1 (d, 1H), 3.87 (s, 3H).

Workup

  1. temperatureheated on a hot plate
  2. customa yellow solid precipitates out of solution
  3. additionAnother 100 mL of methanol are added
  4. temperatureAfter another 15 minutes of heating
  5. temperatureto cool for 5 minutes
  6. filtrationthe product is filtered
  7. washwashed with ether
  8. customAir drying in the funnel overnight

Sources & evidence

ORD record
ord-f4a9c15999324735a1b61d6e4304b449
Source dataset
uspto-grants-1993_06
Patent number
US05216165

Reaction notes

Loading…