Sodium Hydroxide → 4-Chloroisoquinolin-5-amine

HRID 10550

Reaction equation

HRID 10550 reaction equation
O.O.[Sn](Cl)Cl.[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[N+:17]([O-])=O)[CH:10]=[N:9][CH:8]=1.[OH-].[Na+]>Cl>[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[NH2:17])[CH:10]=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 219799674-Chloro-5-nitroisoquinoline

Product 1

HCID 219799374-Chloroisoquinolin-5-amineYield 67.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

Tin(II) chloride dihydrate (1.70 g) was dissolved in concentrated hydrochloric acid (1 ml), added with a mixture of Intermediate 89 (315 mg) and 2 N aqueous hydrochloric acid (2 ml) with ice cooling and refluxed with heating for 2 hours. The reaction mixture was cooled to room temperature, added with 5 N aqueous sodium hydroxide (7 ml) and extracted twice with chloroform (20 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the title compound (182 mg).

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 2 hours
  3. extractionextracted twice with chloroform (20 ml for each time)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fcdc390576094c1d8a9ce9abd10a933f
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Linked notes

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