Phosphorus oxychloride → HCID 17954560, compound

HRID 859987Notes

Reaction equation

HRID 859987 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](O)[CH:8]=[C:7]2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1.O=P(Cl)(Cl)[Cl:24]>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:24])[CH:8]=[C:7]2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516417HCID 178516417, compound

Product 1

HCID 17954560HCID 17954560, compoundYield 38.8%

Procedure

8-Bromo-2-hydroxy-4-(3,4-dichlorophenyl)aminoquinoline (3.52 g, 9.16 mmol) and 26 mL of POCl3 were heated to 120° C. for 4 h. The bulk of the POCl3 was distilled (˜18 mL), and the reaction cooled. The solution was poured slowly onto warm water to get a gummy solid. The water was decanted and the solids washed with several portions of water. A final wash with toluene and drying under vacuum afforded 1.43 g of material (3.55 mmol, 38.8%). 1H NMR (300 MHz, DMSO): 9.58(s, 1H), 8.39(d, 1H, J=8.48 Hz), 8.15(d, 1H, J=7.67 Hz), 7.70(d, 1H, J=8.88 Hz), 7.66(d, 1H, J=2.42 Hz), 7.51(dd, 1H, J=8.48, 7.67 Hz), 7.44(d, 1H, J=8.88, 2.42 Hz), 6.90(s, 1H).

Workup

  1. distillationThe bulk of the POCl3 was distilled (˜18 mL)
  2. temperaturethe reaction cooled
  3. additionThe solution was poured slowly
  4. temperatureonto warm water
  5. customto get a gummy solid
  6. customThe water was decanted
  7. washthe solids washed with several portions of water
  8. washA final wash with toluene
  9. customdrying under vacuum

Sources & evidence

ORD record
ord-5beb755b6acf4ce5b9c69d29d5f117ff
Source dataset
uspto-grants-2006_12
Patent number
US07153865B2

Reaction notes

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