2-benzyl-3,4-dihydro-1H-benzo[b][1,6]naphthyridine → HCID 13193877, compound

HRID 1597274Notes

Reaction equation

HRID 1597274 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=[CH:11][C:10]=2[CH2:9]1)C1C=CC=CC=1>FC(F)(F)C(O)=O.[Pt]=O>[CH2:9]1[NH:8][CH2:17][CH2:16][C:15]2[N:14]=[C:13]3[CH2:18][CH2:19][CH2:20][CH2:21][C:12]3=[CH:11][C:10]1=2

Participants

4

Reactant 1

HCID 38452462-benzyl-3,4-dihydro-1H-benzo[b][1,6]naphthyridine

Product 1

HCID 13193877HCID 13193877, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Platinum oxide (850 mg) was added to a solution of 2-benzyl-1,2,3,4-tetrahydrobenzo[b][1,6]-naphthyridine (8.5 g, 31 mmol) in trifluoroacetic acid (155 ml), and catalytic reduction was carried out at 50° C. for 24 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was made basic with 6N sodium hydroxide and extracted with toluene. The extract solution was dried over anhydrous sodium sulfate, and the organic solvent was removed by concentration under reduced pressure and the residue was recrystallized from isopropyl ether to obtain the desired compound (5.3 g, 90%) as white crystals.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionextracted with toluene
  4. dry with materialThe extract solution was dried over anhydrous sodium sulfate
  5. customthe organic solvent was removed by concentration under reduced pressure
  6. customthe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-aa5c7e82a7c44efcbd03dc11d35164bb
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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