Ammonium Hydroxide → 3-Carbethoxy-4-chloro-6,7-dimethoxylquinoline

HRID 1934913Notes

Reaction equation

HRID 1934913 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1O)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)([O:3][CH2:4][CH3:5])=[O:2].P(Cl)(Cl)([Cl:23])=O.[OH-].[NH4+]>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:23])=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 178469636HCID 178469636, compound

Product 1

HCID 103571783-Carbethoxy-4-chloro-6,7-dimethoxylquinoline

Conditions

Temperature
110 °C

Procedure

A mixture of 28.8 g of 3-carbethoxy-4-hydroxy-6,7-dimethoxyquinoline and 16.6 ml of phosphorous oxychloride was stirred at 110° C. for 30 min, cooled to 0° C., and treated with a mixture of ice and ammonium hydroxide. The resulting grey solid was filtered, washed with water and ether, and dried, mp 147-150° C.

Workup

  1. temperaturecooled to 0° C.
  2. filtrationThe resulting grey solid was filtered
  3. washwashed with water and ether
  4. customdried

Sources & evidence

ORD record
ord-e16f20aa45cb433e92e14449861aafb3
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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