Hydrochloric Acid → HCID 14555937, compound

HRID 649114Notes

Reaction equation

HRID 649114 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]3[CH:26]=[CH:25][C:16]([O:17][CH:18]([CH3:24])[C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=3)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([O:17][CH:18]([CH3:24])[C:19]([OH:21])=[O:20])=[CH:25][CH:26]=3)[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14555936HCID 14555936, compound

Product 1

HCID 14555937HCID 14555937, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-{4-[N-(7-chloroquinolin-3-yl)amino]phenoxy}propionate (370 mg) and potassium hydroxide (200 mg) in methanol (10 ml) was warmed and stirred for 24 hours. The solution was poured into dilute hydrochloric acid (50 ml of 0.5M) and extracted with ethyl acetate (2×50 ml). The organic layer was dried over magnesium sulphate, filtered and evaporated to give 2-{4-[N-(7-chloroquinolin-3-yl)amino]phenoxy}propionic acid (200 mg) as a brown solid, mp 150° C.

Workup

  1. extractionextracted with ethyl acetate (2×50 ml)
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-cbe9e305d95a4df492b3f19100d7f511
Source dataset
uspto-grants-1988_04
Patent number
US04738710

Reaction notes

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