Phosphorus oxychloride → 4-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole

HRID 1042983Notes

Reaction equation

HRID 1042983 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][C:8]=2[O:21][CH3:22])=[C:5]([CH3:23])[O:4][N:3]=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][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[CH3:23])=[C:8]([O:21][CH3:22])[CH:9]=2)[N:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486766HCID 178486766, compound2×

Product 1

HCID 574655804-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazoleYield 94%

Procedure

A suspension of 7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-3-nitro-4-quinolinol (for a preparation see Intermediate 17, 5 g, 16 mmol) in POCl3 (20 ml) was refluxed overnight. After cooling, the mixture was evaporated to dryness. The resulting residue was poured over saturated aqueous Sodium hydrogen carbonate and extracted with DCM. The organic layer was washed with water, dried over Na2SO4. The solvent was evaporated under reduce pressure to give the title compound as a light brown powder (5 g, 94%). 1H NMR (300 MHz, DMSO-d6, ppm) δ: 9.27 (s, 1H), 8.15 (s, 1H), 7.73 (s, 1H), 4.05 (s, 3H), 2.36 (s, 3H), 2.16 (s, 3H).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to dryness
  4. additionThe resulting residue was poured over saturated aqueous Sodium hydrogen carbonate
  5. extractionextracted with DCM
  6. washThe organic layer was washed with water
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f4b91475985e4475b230c46554332e30
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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