Ammonium Hydroxide → 2,7-Dichloro-4-methylquinoline

HRID 1743017Notes

Reaction equation

HRID 1743017 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][C:8](=O)[NH:9]2)=[CH:4][CH:3]=1.[NH4+].[OH-].O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:8]1[CH:7]=[C:6]([CH3:13])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 756802(1H)-Quinolinone, 7-chloro-4-methyl-

Product 1

HCID 1088002,7-Dichloro-4-methylquinolineYield 72%

Procedure

A solution of quinolone 13 (10 g; 51.6 mmol) in 90 ml of POCl3 was refluxed for 2 hours. After cooling, the mixture was poured into 300 g ice-water and neutralized with NH4OH. The resultant precipitate was filtered off and washed with cold H2O. The crude product was recrystallized from 95% ethanol to obtain 8.95 g (72%) of 14. 1H NMR (CDCl3): δ 2.71 (s, 3H); 7.28 (d, 1H); 7.55 (d, 1H); 7.92 (d, 1H); 8.08 (d, 1H).

Workup

  1. temperatureAfter cooling
  2. filtrationThe resultant precipitate was filtered off
  3. washwashed with cold H2O
  4. customThe crude product was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-662460c749184644ab7bbef471ccd891
Source dataset
uspto-grants-1994_08
Patent number
US05342946

Reaction notes

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