Phosphorus oxychloride → HCID 57465578, compound

HRID 1042981Notes

Reaction equation

HRID 1042981 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11](O)=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[N:14]3)=[CH:9][CH:8]=2)=[C:5]([CH3:21])[O:4][N:3]=1.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:11]1[C:10]2[C:15](=[CH:16][C:7]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:21])=[CH:8][CH:9]=2)[N:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178434743HCID 178434743, compound

Product 1

HCID 57465578HCID 57465578, compoundYield 75%

Procedure

A suspension of 7-(3,5-dimethyl-4-isoxazolyl)-3-nitro-4-quinolinol (for a preparation see intermediate 15, 5 g, 17 mmol) in POCl3 (50 ml) was refluxed overnight. After cooling the solvent was evaporated in vacuo. The resulting residue was poured over saturated aqueous Sodium hydrogen carbonate, extracted with DCM, washed with water, dried over Na2SO4. The solvent was evaporated under reduce pressure to give the title compound as a light brown solid (4 g, 75%). 1H NMR (300 MHz, CDCl3, ppm) δ: 9.23 (s, 1H), 8.45 (d, J=8.9 Hz, 1H), 8.04 (d, J=1.5 Hz, 1H), 7.67 (dd, J=8.9, 1.5 Hz, 1H), 2.47 (s, 3H), 2.32 (s, 3H).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling the solvent
  3. customwas evaporated in vacuo
  4. additionThe resulting residue was poured over saturated aqueous Sodium hydrogen carbonate
  5. extractionextracted with DCM
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-fcf879bc50724d63a9fa418f30d41e48
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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