Phosphorus oxychloride → 4-Chloro-3-nitroquinoline

HRID 1672305Notes

Reaction equation

HRID 1672305 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1O)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526762HCID 178526762, compound

Product 1

HCID 112758084-Chloro-3-nitroquinoline

Procedure

5.5 g (29 mmol) 3-nitro-quinolin-4-ol (Example 1a) in 25 ml POCl3 are heated for 2 h to keep at 130° C. The mixture is cooled to rt and poured into ice-water. The precipitate is filtered off, washed with ice-cold water, and dissolved in CH2Cl2. The organic phase is washed with cold 0.1N NaOH (1×) and with cold water (2×). After drying over MgSO4, the solvent is evaporated to dryness. The residue is stirred in hexane. The title compound is isolated as a powder and is dried at 60° C. under vacuum. mp: 121-122° C.; NMR (CDCl3): 9.26/s (1H), 8.44/d and 8.21/d (2H), 7.95/t and 7.82/t (2H); HPLC: tret=1 1.64 min (Grad 1).

Workup

  1. customto keep at 130° C
  2. filtrationThe precipitate is filtered off
  3. washwashed with ice-cold water
  4. dissolutiondissolved in CH2Cl2
  5. washThe organic phase is washed with cold 0.1N NaOH (1×) and with cold water (2×)
  6. dry with materialAfter drying over MgSO4
  7. customthe solvent is evaporated to dryness

Sources & evidence

ORD record
ord-dab3daac2a964ff088eedd0767346550
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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