8-Methyl-7-nitroquinoline → HCID 14115670, compound

HRID 565425Notes

Reaction equation

HRID 565425 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:12][C:3]1[C:2]([CH3:1])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 2541658-Methyl-7-nitroquinolineHCID 2723923Ammonium formate

Product 1

HCID 14115670HCID 14115670, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Amino-8-methylguinoline. To a solution of 1.45 g of 8-methyl-7-nitroquinoline in 20 mL of ethanol are added 1.45 g of ammonium formate and a catalytic amount of 10% palladium-on-carbon. The resulting suspension is stirred at room temperature for 3 hours. The reaction mixture is filtered on Celite, with a methanol wash of the solids, and the filtrate is rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 50% ethyl acetate/hexanes followed by recrystallization from hexanes/methylene chloride to provide 1.10 g of 7-amino-8-methylquinoline as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture is filtered on Celite, with a methanol
  2. washwash of the solids
  3. customThe residue is purified by flash column chromatography on silica gel
  4. washeluting with 50% ethyl acetate/hexanes
  5. customfollowed by recrystallization from hexanes/methylene chloride

Sources & evidence

ORD record
ord-9d8edb6dbcb74b419a22cc9afe9ea6ed
Source dataset
uspto-grants-2001_01
Patent number
US06172095B2

Reaction notes

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