Tetrahydrofuran → 4-Bromo-7-isoquinolinamine

HRID 1173118Notes

Reaction equation

HRID 1173118 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.O1CCCC1.[Cl-].[NH4+].[OH-].[Na+]>C(O)C.[Fe].O>[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 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 22674041HCID 22674041, compound

Product 1

HCID 226740574-Bromo-7-isoquinolinamineYield 56.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe resulting residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-55d99ed0bf664372b1486baab47e5983
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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