3-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-methyl-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one → HCID 13189028, compound

HRID 1995299Notes

Reaction equation

HRID 1995299 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][C:15]3[C:18]4[CH:26]=[C:25]([N+:27]([O-])=O)[C:24]([CH3:30])=[CH:23][C:19]=4[O:20][C:21](=[O:22])[C:14]=3[CH2:13]1)[CH2:2]2.[H][H]>CN(C)C=O.[Ni]>[NH2:27][C:25]1[C:24]([CH3:30])=[CH:23][C:19]2[O:20][C:21](=[O:22])[C:14]3[CH2:13][N:12]([CH2:11][CH2:10][N:3]4[CH2:2][CH:1]5[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]5)[CH2:4]4)[CH2:17][CH2:16][C:15]=3[C:18]=2[CH:26]=1

Participants

5

Reactant 2

HCID 131890193-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-methyl-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 13189028HCID 13189028, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[2-(3-azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-methyl-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one (10.5 g, 0.026 moles) in N,N-dimethylformamide (300 ml) is hydrogenated at 50 psi at 24° C. in the presence of Raney Nickel until the required amount of hydrogen has been taken up. The catalyst is filtered off and rinsed with hot N,N-dimethylformamide until free of organic material. The filtrate is slightly concentrated and cooled to give the product. Recrystallization from ethanol gave the product (5.1 g), mp 142°-143° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. washrinsed with hot N,N-dimethylformamide until free of organic material
  3. concentrationThe filtrate is slightly concentrated
  4. temperaturecooled
  5. customto give the product
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-1952acfb182b490093d9c01366d0964b
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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