Ethanol → 6-Amino-4,5,8-trimethylquinoline

HRID 1901465Notes

Reaction equation

HRID 1901465 reaction equation
[N+:1]([C:4]1[C:5]([CH3:16])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH3:15])([O-])=O.O.O.[Sn](Cl)Cl.C(O)C.[OH-].[Na+]>O>[NH2:1][C:4]1[C:5]([CH3:16])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH3:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 105606624,5,8-Trimethyl-6-nitroquinoline

Product 1

HCID 153800186-Amino-4,5,8-trimethylquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-nitro-4,5,8-trimethylquinoline (0.60 g), tin(II)chloride dihydrate (3.13 g), and ethanol (40 mL) is heated for 3 hours at 60°-65° C. and then cooled to room temperature. 10% Aqueous sodium hydroxide (24 mL) and water (48 mL) are added, and the mixture is extracted three times with chloroform. The combined organic layers are washed with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered and evaporated to afford a crude product. The crude product is purified by flash chromatography using 25% ethyl acetate in hexane as eluent, providing 6-amino-4,5,8-trimethylquinoline.

Workup

  1. temperatureis heated for 3 hours at 60°-65° C.
  2. extractionthe mixture is extracted three times with chloroform
  3. washThe combined organic layers are washed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a crude product
  8. customThe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-b7cb0d2c55c1455391da6faebe32e7c7
Source dataset
uspto-grants-1996_11
Patent number
US05578607

Reaction notes

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