Hydrochloric Acid → HCID 178516402, compound

HRID 859986Notes

Reaction equation

HRID 859986 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([OH:12])[CH:8]=[C:7]2O.[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1Cl)[NH2:18].[ClH:23]>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([OH:12])[CH:8]=[C:7]2[NH:18][C:17]1[CH:19]=[CH:20][CH:21]=[C:15]([Cl:14])[C:16]=1[Cl:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 72573,4-DichloroanilineHCID 178418887HCID 178418887, compound

Product 1

HCID 178516402HCID 178516402, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Prepared using general procedure 1; 8-Bromo-2,4-quinolinediol (4 g, 16.66 mmol), 3,4-dichloroaniline (8 g, 49.38 mmol), 2.78 mL of 6 M HCl (16.68 mmol) and 20 mL NMP were irradiated to achieve 200° C. (400 W max) for 30 min. Cooling and precipitation by pouring onto 100 mL water afforded 3.52 g of product (9.16 mmol, 55%). 1H NMR (300 MHz, DMSO): 9.77(s, 2H), 8.95(s, 1H), 8.11(dd, 1H, J=8.48, 0.81 Hz), 7.89(dd, 1H, J=7.67, 0.81 Hz), 7.66(d, 1H, J=8.88 Hz), 7.58(d, 1H, J=2.42 Hz), 7.36(dd, 2H, J=8.48, 2.42 Hz), 7.20(t, 1H, J=8.07 Hz), 5.88(s, 1H).

Workup

  1. customPrepared
  2. customto achieve 200° C.
  3. customfor 30 min
  4. temperatureCooling
  5. customprecipitation
  6. additionby pouring onto 100 mL water

Sources & evidence

ORD record
ord-d5830b8712bc4b62bc3117b98b92aa56
Source dataset
uspto-grants-2006_12
Patent number
US07153865B2

Reaction notes

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