1-Pentanol → 1,6-Naphthyridin-3-amine

HRID 887673Notes

Reaction equation

HRID 887673 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:12]=2[CH:13]=1)([O-])=O.C(O)CCCC>CO.[Pd]>[N:6]1[C:7]2[C:12](=[CH:11][N:10]=[CH:9][CH:8]=2)[CH:13]=[C:4]([NH2:1])[CH:5]=1

Participants

5

Reactant 2

HCID 62761-PentanolHCID 142970643-Nitro-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 1

HCID 207188471,6-Naphthyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

3-Nitro-5,6,7,8-tetrahydro-[1,6]naphthyridine (1 g, 5.6 mmol), pentanol (2 mL) and Pd/C (300 mg) were placed in a microwave reaction vessel and stirred under microwave irradiation at 180° C. for 1 h. After cooling, the mixture was diluted with MeOH and filtered through a pad of Celite. The solvent was removed and the crude was purified by flash column chromatography to give the desired title compound as a yellow solid. MS (ES+): 146.2 (M+H)+. Calc'd for C8H7N3—145.06.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered through a pad of Celite
  3. customThe solvent was removed
  4. customthe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-e5fd5af32fea4fb88f25cb00a9a98db4
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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