Ammonia → 4-Chloro-5-nitroisoquinoline

HRID 10549

Reaction equation

HRID 10549 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[N+:12]([O-])([O-:14])=[O:13].[K+].N>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:12]([O-:14])=[O:13])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24434Potassium NitrateHCID 6409744-Chloroisoquinoline

Product 1

HCID 219799674-Chloro-5-nitroisoquinolineYield 69.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Intermediate 88 (375 mg) was dissolved in concentrated sulfuric acid (2 ml), then added with potassium nitrate (260 mg) with ice cooling and stirred for 2 hours. The reaction mixture was added with 28% aqueous ammonia (10 ml) and extracted twice with ethyl acetate (15 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (332 mg).

Workup

  1. extractionextracted twice with ethyl acetate (15 ml for each time)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d8ae3de07dce41eb80afac012049edb2
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Linked notes

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