Stannous Chloride → 1-Chloro-6-methylisoquinolin-5-amine

HRID 1042249

Reaction equation

HRID 1042249 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[C:14]2[C:9](=[C:10]([N+:16]([O-])=O)[C:11]([CH3:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7][N:6]=1>C(O)C.C(Cl)Cl.C(Cl)Cl>[Cl:4][C:5]1[C:14]2[CH:13]=[CH:12][C:11]([CH3:15])=[C:10]([NH2:16])[C:9]=2[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 226222211-Chloro-6-methyl-5-nitroisoquinoline

Product 1

HCID 596273751-Chloro-6-methylisoquinolin-5-amineYield 40.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584144Dichloromethane ethanolSolvent

Conditions

Temperature
70 °C

Procedure

Tin (II) chloride (0.43 g, 2.2 mmol) was added to a solution of 1-chloro-6-methyl-5-nitroisoquinoline (0.100 g, 0.45 mmol) in ethanol/DCM (10.0 mL, 4:1). The solution was heated at 70° C. for 16 h. The reaction mixture was diluted with DCM and the organic phase was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown solid which was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford 1-chloro-6-methylisoquinolin-5-amine (0.035 g, 40% yield) as a brown solid. MS (ESI, pos. ion) m/z: 193 [M+H]+

Workup

  1. washthe organic phase was washed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a brown solid which
  6. customwas purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d8de82e3eeb9429bb135be4b66ab8ddd
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Linked notes

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