Phosphorus oxychloride → HCID 18505063, compound

HRID 1437150Notes

Reaction equation

HRID 1437150 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12]1[C:13](=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:14](O)=O.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:14]1[C:13]2[C:12]([N:11]=[C:3]3[C:4]=1[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=[C:2]3[CH3:1])=[CH:20][CH:19]=[C:18]([O:21][CH3:22])[CH:17]=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18505064HCID 18505064, compound

Product 1

HCID 18505063HCID 18505063, compoundYield 68%

Procedure

N-(2′-methyl-5′-nitrophenyl)-5-methoxyanthranilic acid (7.2 g) is heated in phosphorous oxychloride (60 ml) at 120° C. for 1 hour. Excess phosphorous oxychloride is distilled off under reduced pressure, and the residue is poured slowly into a stirred mixture of chloroform, concentrated ammonium hydroxide and ice. The separated chloroformic layer is washed with water and dried using magnesium sulfate. Chloroform is evaporated to dryness, and the residue is crystallized from benzene to give 9-chloro-7-methoxy-4-methyl-1-nitroacridine (6.1 g, 68% yield), m.p. 227-228° C. 1H NMR (d6DMSO): δ 8.23 (d, 1H, J=9.3 Hz), 8.13 (d, 1H, J=7.3 Hz), 7.79 (bd, 1H, J=8.3 Hz), 7.71 (dd, 1H, J1=9.3 Hz, J2=2.9 Hz), 7.58 (d, 1H, J=2.9 Hz), 4.02 (s, 3H), 2.85 (s, 3H).

Workup

  1. distillationExcess phosphorous oxychloride is distilled off under reduced pressure
  2. additionthe residue is poured slowly into a stirred mixture of chloroform, concentrated ammonium hydroxide and ice
  3. washThe separated chloroformic layer is washed with water
  4. customdried
  5. customChloroform is evaporated to dryness
  6. customthe residue is crystallized from benzene

Sources & evidence

ORD record
ord-8cd6cdc5bca34f10930c277e0a7335aa
Source dataset
uspto-grants-2009_11
Patent number
US07622478B2

Reaction notes

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