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

HRID 1416897Notes

Reaction equation

HRID 1416897 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+]>CO.[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, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-methyl-7-nitroquinoline (1.8 g) in methanol (20 mL) is added palladium-on-carbon (10%, 0.45 g) and ammonium formate (2.77 g). The mixture is stirred at room temperature for 30 minutes, then filtered on Celite, with a methanol wash of the solids. The filtrate is rotary evaporated and the residue partitioned between water and methylene chloride. The organic layer is dried over potassium carbonate, filtered and rotary evaporated to afford 7-amino-8-methylquinoline as a yellow solid.

Workup

  1. filtrationfiltered on Celite, with a methanol
  2. washwash of the solids
  3. customThe filtrate is rotary evaporated
  4. customthe residue partitioned between water and methylene chloride
  5. dry with materialThe organic layer is dried over potassium carbonate
  6. filtrationfiltered
  7. customrotary evaporated

Sources & evidence

ORD record
ord-b220c06f3c6042068270816a5513ab96
Source dataset
uspto-grants-1999_06
Patent number
US05916900

Reaction notes

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