Sodium Hydroxide → HCID 11759092, compound

HRID 397303Notes

Reaction equation

HRID 397303 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10](O)[C:9]2[C:4](=[C:5]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:23])=O.[OH-].[Na+]>>[CH3:1][C:2]1[CH:11]=[C:10]([Cl:23])[C:9]2[C:4](=[C:5]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178428813HCID 178428813, compound

Product 1

HCID 11759092HCID 11759092, compound

Procedure

A mixture of intermediate (9) (1.32 g) and phosphorous oxychloride (5 ml) was refluxed for 2 hours, cooled, poured onto ice and neutralized by 1N NaOH. The aqueous layer was extracted by ethyl acetate. The organic layer was washed with brine, dried, concentrated, yielding 2-methyl-4-chloro-8-(2′,4′-dichlorophenyl)quinoline (intermediate 1) (1.31 mg. 300 MHz 1H NMR (CDCl3): δ 2.58 (s,3H), 7.34 (s,2H), 7.39 (s,1H), 7.53 (s,1H), 7.63-7.65 (m,2H), 8.26 (dd, 1H).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturecooled
  3. additionpoured onto ice
  4. extractionThe aqueous layer was extracted by ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-346b9ab8b32044d78b08700ccf7ba755
Source dataset
uspto-grants-2003_08
Patent number
US06610678B2

Reaction notes

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