4-Chlorobenzoic Acid → HCID 14802297, compound

HRID 1680954Notes

Reaction equation

HRID 1680954 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH3:15])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([Cl:12])=[CH:7]2.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=O)=[CH:19][CH:18]=1.[OH-].[Na+]>>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]2[N:13]([CH2:14][CH3:15])[C:3]3[CH:4]=[CH:5][C:6]4[CH:7]=[C:8]([Cl:12])[CH:9]=[N:10][C:11]=4[C:2]=3[N:1]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 63184-Chlorobenzoic AcidHCID 14798Sodium HydroxideHCID 15023099HCID 15023099, compound

Product 1

HCID 14802297HCID 14802297, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 4.1 g (20 mmol) of 8-amino-3-chloro-7-ethylaminoquinoline, 3.1 g (20 mmol) of 4-chlorobenzoic acid and 20 ml of polyphosphoric acid is heated at 120° C. for 1 hour. It is allowed to cool to 90° C., and 100 g of ice are slowly added to the solution. The mixture is then poured into 200 g of ice, and the pH is adjusted to 12 with concentrated sodium hydroxide solution. The precipitate is filtered off with suction, washed thoroughly with hot water, dried at 70° C. under reduced pressure and recrystallized from ethyl acetate.

Workup

  1. temperatureto cool to 90° C.
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed thoroughly with hot water
  4. customdried at 70° C. under reduced pressure
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a004dd77b2a84f13b66a9e8a9355ea95
Source dataset
uspto-grants-1992_12
Patent number
US05167695

Reaction notes

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