Acetic Acid → HCID 15540958, compound

HRID 1597275Notes

Reaction equation

HRID 1597275 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.C(O)(=O)C>CO.[C].[Pd]>[CH2:9]1[NH:8][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]1=2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 38452462-benzyl-3,4-dihydro-1H-benzo[b][1,6]naphthyridine

Product 1

HCID 15540958HCID 15540958, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-Benzyl-1,2,3,4-tetrahydro-benzo[b][1,6]-naphthyridine (4.4 g, 16.04 mmol) was dissolved in methanol (88 ml), followed by adding thereto acetic acid (1.84 ml, 32.08 mmol) and palladium-carbon (440 mg), and catalytic reduction was carried out overnight at 50° C. The catalyst was filtered off and the filtrate was neutralized with potassium carbonate and filtered. The organic layer thus obtained was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (methylene chloride/methanol=30/1 to 10/1) to obtain the desired compound (1.1 g, 37.2%) as a brown solid.

Workup

  1. additionby adding
  2. filtrationThe catalyst was filtered off
  3. filtrationfiltered
  4. customThe organic layer thus obtained
  5. concentrationwas concentrated under reduced pressure
  6. customthe residue was purified by a silica gel column chromatography (methylene chloride/methanol=30/1 to 10/1)

Sources & evidence

ORD record
ord-edc7b296957f4d128d5595cbff2a157a
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

Loading…