Acetic Acid → HCID 13386235, compound

HRID 647427Notes

Reaction equation

HRID 647427 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Br.C(O)(=O)C>O>[Cl:1][C:2]1[N:3]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 13386234HCID 13386234, compound

Product 1

HCID 13386235HCID 13386235, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-chloro-1-[N-(4-methoxyphenyl)amino]isoquinoline (1.90 g), hydrogen bromide (10 ml of 48%) and glacial acetic acid was heated under reflux for a period of 9.5 hours. The reaction mixture was poured into water, and the aqueous mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure to give 4-[N-(3-chloroisoquinolin-1-yl)amino]phenol (1.84 g) as pale yellow crystals mp 170° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 9.5 hours
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-57c3f871e3294e5882cb5e2c7c4fc706
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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