HCID 8966164, compound → 10-Phenyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine

HRID 1597286Notes

Reaction equation

HRID 1597286 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]3=[C:11]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10]=2[CH2:9]1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[C:22]1([C:11]2[C:10]3[CH2:9][NH:8][CH2:17][CH2:16][C:15]=3[N:14]=[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=23)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 8966164HCID 8966164, compound

Product 1

HCID 1846204910-Phenyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridineYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Palladium black (125 mg) was added to a solution of 2-benzyl-10-phenyl-1,2,3,4-tetrahydro-benzo[b][1,6]-naphthyridine (1.25 g, 3.57 mmol) in acetic acid (9 ml), and the resulting mixture was stirred under a hydrogen atmosphere for 9 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was made basic with 1N sodium hydroxide and extracted with diethyl ether. The extract solution was dried over anhydrous sodium sulfate and concentrated under reduced pressured to be freed of the solvent, and the residue was washed with diethyl ether to obtain the desired compound (0.45 g, 1.75 mmol, 49%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionextracted with diethyl ether
  4. dry with materialThe extract solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressured
  6. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-51e52849eb354389beeb5b949dad2da1
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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