Stannous chloride dihydrate → 2-Methylquinolin-6-amine

HRID 1642347Notes

Reaction equation

HRID 1642347 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=2)[N:3]=1.O.O.Cl[Sn]Cl>Cl>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:12])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 691722-Methyl-6-nitroquinoline

Product 1

HCID 1031482-Methylquinolin-6-amineYield 68.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of 2-methyl-6-nitroquinoline (12 g, 63.84 mmol) in HCl (1N, 450 mL) was added a solution of SnCl2.2H2O (72 g, 0.32 mol) in HCl (1N, 150 mL) slowly. The reaction mixture was heated to reflux for 15 min, then cooled to room temperature. The precipitate was filtered. The filtrate was basified by aqueous KOH and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to give 6.9 g of 2-methylquinolin-6-amine (68.3%). MS[M++1]=159, LC-MS: tR=0.255 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 15 min
  3. filtrationThe precipitate was filtered
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c7ee4eb12067497e8f1d2811693fe536
Source dataset
uspto-grants-2012_02
Patent number
US08119660B2

Reaction notes

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