Sodium Hydroxide → 6-Aminoisoquinoline

HRID 1845940Notes

Reaction equation

HRID 1845940 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.O.[NH3:13].[OH-].[Na+]>ClCCl.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[NH2:13][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 3136816-BromoisoquinolineHCID 12896473Azane;hydrate

Product 1

HCID 5889916-Aminoisoquinoline

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
190 °C

Procedure

6-bromoisoquinoline that weighed 17.2 g (see WO 2008/077553), 200 mL of 28% ammonia water and 10.8 g of copper (II) sulfate pentahydrate were put into the autoclave and tightly sealed, and the mixture was then stirred at 190° C. for 6 hours. After cooling to room temperature, the reaction solution was poured into 250 mL of a 10% aqueous sodium hydroxide solution, followed by extraction with ethyl acetate (100 mL×5). The extract was dried over anhydrous sodium sulfate, filtered, and then concentrated. The obtained crude product was suspended in dichloromethane and then filtered to obtain 10.2 g of the compound of interest as a light brown crystal (85%).

Workup

  1. customtightly sealed
  2. temperatureAfter cooling to room temperature
  3. extractionfollowed by extraction with ethyl acetate (100 mL×5)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe obtained crude product
  8. filtrationfiltered

Sources & evidence

ORD record
ord-be5bc267eeed4a338635cf04d78ed03a
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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