4-[(1,7-Dichloro-3-isoquinolinyl)methylamino]phenol → HCID 13386231, compound

HRID 647421Notes

Reaction equation

HRID 647421 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:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH3:14])[N:3]=1>C(O)(=O)C.O.[Zn]>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[C:4]([N:13]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[CH3:14])[N:3]=[CH:2]2)=[CH:7][CH:8]=1

Participants

5

Reactant 1

HCID 133862264-[(1,7-Dichloro-3-isoquinolinyl)methylamino]phenol

Product 1

HCID 13386231HCID 13386231, compoundYield 39.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Zinc powder (0.63 g) was added portionwise to a solution of 4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]phenol (2.82 g) in a mixture of acetic acid (135 ml) and water (15 ml). On completion of the addition the mixture was heated under reflux for a period of 1 hour and was then filtered to remove any residual zinc. The solvent was removed by distillation under reduced pressure to give an oil. The oil was purified by chromatography over silica gel (eluant dichloromethane/ethyl acetate; 90:10) to give 4-[N-(7-chloroisoquinolin-3-yl)-N-methylamino]phenol (1.0 g) as an orange solid mp 140° C.

Workup

  1. additionOn completion of the addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for a period of 1 hour
  4. filtrationwas then filtered
  5. customto remove any residual zinc
  6. customThe solvent was removed by distillation under reduced pressure
  7. customto give an oil
  8. customThe oil was purified by chromatography over silica gel (eluant dichloromethane/ethyl acetate; 90:10)

Sources & evidence

ORD record
ord-7a10d19402494e3c891bc537611e907d
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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