Sodium Chloride → 4-Bromo-7-isoquinolinamine

HRID 1005676Notes

Reaction equation

HRID 1005676 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([Br:14])=[CH:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].[Cl-].[Na+]>C(O)C.O1CCCC1.O.[Fe]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([Br:14])=[CH:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1

Participants

8

Reactant 3

HCID 5234Sodium ChlorideHCID 25517Ammonium ChlorideHCID 22674041HCID 22674041, compound

Product 1

HCID 226740574-Bromo-7-isoquinolinamineYield 56.9%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 1 ml of ethanol, 2 ml of tetrahydrofuran and 1 ml of water was dissolved 66 mg (0.26 mmol) of 7-nitro-4-bromoisoquinoline, and 70 mg of powdered iron and 140 mg of ammonium chloride were added thereto, followed by heating at 50 degrees for 3 hours. To the reaction mixture was added 1 N sodium chloride aqueous solution, followed by extracting with chloroform. The organic layer was dried over magnesium sulfate and concentrated. Then, the resulting residue was crystallized from isopropyl ether, to give 33 mg of the title compound.

Workup

  1. additionwere added
  2. temperatureby heating at 50 degrees for 3 hours
  3. extractionby extracting with chloroform
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThen, the resulting residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-857f900068b04f0ab88ac8ee3edf31cd
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

Loading…