Phosphorus oxychloride → HCID 66880085, compound

HRID 476157Notes

Reaction equation

HRID 476157 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2O.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=2)[N:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178423389HCID 178423389, compound2×

Product 1

HCID 66880085HCID 66880085, compound

Procedure

6-Methyl-3-nitroquinolin-4-ol (Compound of step 2, 610 mg) in POCl3 (5 mL) was stirred for 45 min at 120° C. The mixture was cooled to RT and poured slowly into ice-water. The precipitate was filtered, washed with ice-cold water and dissolved in CH2Cl2. The organic phase was washed with cold brine, and the aqueous phase was discarded. After drying over Na2SO4, the organic solvent was evaporated to dryness to obtain the title compound. Yield: 600 mg (90%); 1HNMR (DMSO-d6, 300 MHz: δ 9.299 (s, 1H), 8.192 (s, 1H,), 8.096-8.124 (d, 1H, J=8.4 Hz), 7.893-7.927 (dd, 1H, J=8.4 Hz, 1.8 Hz), 2.604 (s, 3H).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ice-cold water
  3. dissolutiondissolved in CH2Cl2
  4. washThe organic phase was washed with cold brine
  5. dry with materialAfter drying over Na2SO4
  6. customthe organic solvent was evaporated to dryness

Sources & evidence

ORD record
ord-cdc530f382fa4ddc910582e8b4a557f0
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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