2-Amino-3-nitro-8-methylquinoline → 2,3-Diamino-8-methylquinoline

HRID 133089Notes

Reaction equation

HRID 133089 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1>CO.O1CCCC1.[Pd]>[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 179798462-Amino-3-nitro-8-methylquinoline2×

Product 1

HCID 179798392,3-Diamino-8-methylquinolineYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

0.4 g of palladium on active carbon (5% Pd) is added to a solution of 1.1 g of 2-amino-3-nitro-8-methylquinoline (compound B1) in 50 ml of methanol/tetrahydrofurane 1:1 and the resulting suspension is hydrated for 1 h. The catalyst is filtered off and the filtrate is evaporated in vacuo. The residue is chromatographed on silica gel using dichloromethane/methanol 10:1 to give 0.79 g of the title compound as colourless solid.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated in vacuo
  3. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-36d47d233a1c43da84c954c914752c10
Source dataset
uspto-grants-2008_06
Patent number
US07390819B2

Reaction notes

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