HCID 66778542, compound → HCID 56847101, compound

HRID 1771839Notes

Reaction equation

HRID 1771839 reaction equation
[ClH:1].C([N:9]1[CH2:18][CH2:17][C:16]2[N:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:13]=[CH:12][C:11]=2[CH2:10]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[ClH:1].[N:15]1[C:16]2[CH2:17][CH2:18][NH:9][CH2:10][C:11]=2[CH:12]=[CH:13][C:14]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

4

Reactant 1

HCID 66778542HCID 66778542, compound

Product 1

HCID 56847101HCID 56847101, compoundYield 112.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The crude methyl 6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylate hydrochloride (1.20 g, 3.76 mmol) was dissolved in MeOH (100 mL) and thoroughly degassed. Palladium hydroxide (0.185 g, 1.32 mmol) was added to the solution before being purged with H2 gas three times. The reaction was allowed to stir at rt for 13 h under 1 atm of H2 gas. The mixture was then filtered through a pad of Celite and rinsed with EtOH. The filtrate was then concentrated down to yield methyl 5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylate hydrochloride (0.97 g, 100%). LC-MS: (FA) ES+ 220; 1H NMR (Methanol-d4, 400 MHz) δ 8.05 (d, J=8.0 Hz, 1 H), 7.89 (d, J=8.0 Hz, 1 H), 4.52 (s, 2 H), 3.98 (s, 3 H), 3.66 (t, J=6.5 Hz, 2 H), 3.33 (m, 2 H).

Workup

  1. customthoroughly degassed
  2. custombefore being purged with H2 gas three times
  3. filtrationThe mixture was then filtered through a pad of Celite
  4. washrinsed with EtOH
  5. concentrationThe filtrate was then concentrated down

Sources & evidence

ORD record
ord-9a3342ef86264b65a06da0e706dd265e
Source dataset
uspto-grants-2016_02
Patent number
US09249142B2

Reaction notes

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