Sodium Carbonate → 5-Amino-1-chloroisoquinoline

HRID 2102966Notes

Reaction equation

HRID 2102966 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O>[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([NH2:12])[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 4597741-Chloro-5-nitroisoquinoline

Product 1

HCID 4597715-Amino-1-chloroisoquinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-chloro-5-nitroisoquinoline (450 mg, 0.0022 mol), stannous chloride dihydrate (2.4 g, 0.011 mol), and EtOAc (50 mL) was stirred under reflux under an atmosphere of nitrogen for 3 h. After cooling, the mixture was poured into ice-water and basified to pH 10.0 with aq. Na2CO3. The organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the product as a light yellow solid. LC-MS: 3.17 min, 179.2 & 181.2 (M+1).

Workup

  1. temperatureunder reflux under an atmosphere of nitrogen for 3 h
  2. temperatureAfter cooling
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a099b9b5adda408796e9cb3c2a911cdb
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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