6-Methyl-3-nitro-5,6,7,8-tetrahydro-1,6-naphthyridine → 3-Amino-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine

HRID 1066768Notes

Reaction equation

HRID 1066768 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[CH:5][C:4]=2[CH2:3]1>CO.[Pd]>[NH2:12][C:6]1[CH:7]=[N:8][C:9]2[CH2:10][CH2:11][N:2]([CH3:1])[CH2:3][C:4]=2[CH:5]=1

Participants

4

Reactant 1

HCID 142970606-Methyl-3-nitro-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 1

HCID 117449583-Amino-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-Methyl-3-nitro-5,6,7,8-tetrahydro[1,6]naphthyridine (2.72 g, 1.41 mmol) was dissolved in methanol (100 ml) and treated with 10% palladium on carbon (1.0 g). The mixture was hydrogenated for 2 h. The catalyst was removed by filtration through Celite, the filter bed washed with methanol and the filtrate evaporated to dryness under reduced pressure to give a yellow solid, which was triturated under diethyl ether and the solids collected by filtration, washed with diethyl ether and dried in vacuo (1.89 g, 83%)

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter bed washed with methanol
  3. customthe filtrate evaporated to dryness under reduced pressure
  4. customto give a yellow solid, which
  5. customwas triturated under diethyl ether
  6. filtrationthe solids collected by filtration
  7. washwashed with diethyl ether
  8. customdried in vacuo (1.89 g, 83%)

Sources & evidence

ORD record
ord-a125e8ccd5cb42348a1a4240cc00bad9
Source dataset
uspto-grants-2001_06
Patent number
US06245778B1

Reaction notes

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