Toluene → HCID 20484930, compound

HRID 647438Notes

Reaction equation

HRID 647438 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[CH:5]=[C:4]([N:13]([C:15]2[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23]CC)=[O:22])=[CH:17][CH:16]=2)[CH3:14])[N:3]=1.[CH3:29][O-:30].[Na+].C1(C)C=CC=CC=1>O>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[C:4]([N:13]([C:15]3[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([OH:23])=[O:22])=[CH:17][CH:16]=3)[CH3:14])[N:3]=[C:2]2[O:30][CH3:29])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 10942334Sodium MethoxideHCID 13386227HCID 13386227, compound

Product 1

HCID 20484930HCID 20484930, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-{4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (1.25 g), sodium methoxide (0.63 g) and toluene was heated under reflux for 4 hrs. The mixture was cooled, poured into water and extracted with ethyl acetate. The organic fraction was dried (MgSO4) and evaporated to give 2-{4-[N-(7-chloro-1-methoxyisoquinolin-3-yl)-N-methylamino]phenoxy}propionic acid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hrs
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic fraction was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f9fb191442ab4f8aa4d8c8aa8c19a5f8
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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