Water → 2-Methylquinolin-6-amine

HRID 1935619Notes

Reaction equation

HRID 1935619 reaction equation
O.O.[Sn](Cl)Cl.[CH3:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:17]([O-])=O)[CH:13]=2)[N:8]=1.O.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=2)[N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 691722-Methyl-6-nitroquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 1031482-Methylquinolin-6-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride dihydrate (60.4 g, 0.27 mol) and 2-methyl-6-nitroquinoline (8.4, 44.6 mmol) are stirred in ethanol and the mixture heated at reflux overnight. After cooling to room temperature, DI water (1.2 mL) is added and the solution made basic with sodium bicarbonate. The mixture is extracted with ethyl acetate (3×250 mL) and the combined organics dried (Na2SO4) and filtered. Solvent is evaporated to give a solid which is recrystallized from CH2Cl2 to give the title compound as crystals, 6.2 g (88%); mp187-189° C.; Anal. Calcd for C10H10 N2: C, 75.92; H, 6.37; N, 17.71. Found: C, 75.88; H, 6.35; N, 17.60.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. extractionThe mixture is extracted with ethyl acetate (3×250 mL)
  4. dry with materialthe combined organics dried (Na2SO4)
  5. filtrationfiltered
  6. customSolvent is evaporated
  7. customto give a solid which
  8. customis recrystallized from CH2Cl2

Sources & evidence

ORD record
ord-57c4605e56c0442a8b2e8df5d9597c25
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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