Hydrochloric Acid → HCID 178516416, compound

HRID 859984Notes

Reaction equation

HRID 859984 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[CH:6]=[C:5]2O.[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[Cl:22])[NH2:18].Cl>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[CH:6]=[C:5]2[NH:18][C:17]1[CH:19]=[CH:20][C:21]([Cl:22])=[C:15]([Cl:14])[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 72573,4-DichloroanilineHCID 178516548HCID 178516548, compound

Product 1

HCID 178516416HCID 178516416, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared using general procedure 1; 6-Bromo-2,4-quinolinediol (3 g, 12.5 mmol), 3,4-dichloroaniline, 6.25 mL of 2 M HCl in Et2O were irradiated to 180° C. (400 W max) for 40 min. to afford 1.94 g (5.05 mmol, 40%). 1H NMR (300 MHz, DMSO): 11.36 (s, 1H), 8.83(s, 1H), 8.28(s, 1H), 7.70(dd, 1H, J=8.88, 1.61 Hz), 7.64(d, 1H, J=8.88 Hz), 7.55(d, 1H, J=2.02 Hz), 7.33(dd, 1H, J=8.88, 2.42 Hz), 7.25(d, 1H, J=8.88 Hz), 5.86(s, 1H).

Workup

  1. customPrepared
  2. customto afford 1.94 g (5.05 mmol, 40%)

Sources & evidence

ORD record
ord-830213a3b66941eb898df0d0282afcb4
Source dataset
uspto-grants-2006_12
Patent number
US07153865B2

Reaction notes

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