Hydrochloric Acid → 5,6,7,8-Tetrahydro-1,7-naphthyridine hydrochloride

HRID 82260Notes

Reaction equation

HRID 82260 reaction equation
C([N:8]1[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:18].[H][H]>O1CCOCC1.[Pd]>[ClH:18].[N:15]1[C:16]2[CH2:17][NH:8][CH2:9][CH2:10][C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 113335787-Benzyl-5,6,7,8-tetrahydro-1,7-naphthyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 717209415,6,7,8-Tetrahydro-1,7-naphthyridine hydrochlorideYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A methanolic solution (25 mL) of 7-Benzyl-5,6,7,8-tetrahydro-[1,7]naphthyridine (J. Het. Chem. 2001, 38, 535) (1.5 g, 6.69 mmol) was degassed with argon for 20 min followed by the addition of 4N HCl in dioxane (2 mL) and Pd/C (300 mg, 20 wt %) and stirred under 50 psi hydrogen pressure at room temperature for 24 h. After completion of the reaction the mixture was filtered on a short pad of celite and washed with methanol (4×25 mL). The filtrate was evaporated to dryness in vacuo and crystallized from methanol to afford the title compound as yellowish solid in 65% yield (calculated as 2HCl salt), 900 mg.

Workup

  1. customAfter completion of the reaction the mixture
  2. filtrationwas filtered on a short pad of celite
  3. washwashed with methanol (4×25 mL)
  4. customThe filtrate was evaporated to dryness in vacuo
  5. customcrystallized from methanol

Sources & evidence

ORD record
ord-b559656cc0de40b08b2fc17c4fa39651
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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