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

HRID 1901241Notes

Reaction equation

HRID 1901241 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 Pd/C (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 methanol wash of the solids. The filtrate is rotary evaporated and the residue partitioned between H2O and CH2Cl2. 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 methanol
  2. washwash of the solids
  3. customThe filtrate is rotary evaporated
  4. customthe residue partitioned between H2O and CH2Cl2
  5. dry with materialThe organic layer is dried over potassium carbonate
  6. filtrationfiltered
  7. customrotary evaporated

Sources & evidence

ORD record
ord-919c70c680954da5b67fc9d1a2bd54de
Source dataset
uspto-grants-1996_11
Patent number
US05576437

Reaction notes

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