HCID 13136924, compound → HCID 13136926, compound

HRID 851198Notes

Reaction equation

HRID 851198 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]2[C:11]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]=3[C:17](=[O:19])[O:18][C:4]=2[CH:3]=1.[H][H]>CN(C)C=O.CO.[Ni]>[NH2:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]2[O:18][C:17](=[O:19])[C:12]3[CH2:13][NH:14][CH2:15][CH2:16][C:11]=3[C:5]=2[CH:6]=1

Participants

6

Reactant 2

HCID 13136924HCID 13136924, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13136926HCID 13136926, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalyst2×HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1,2,3,4-tetrahydro-8-methyl-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one (6.0 g, 0.023 moles) in N,N-dimethylformamide (100 ml) and methanol (50 ml) is hydrogenated at 50 psi in the presence of Raney Nickel (0.5 g) at room temperature for 20 hours. Additional Raney Nickel (0.5 g) in N,N-dimethylformamide (50 ml) is then added, and hydrogenation resumed until hydrogen uptake ceases. The catalyst is filtered off and rinsed with warm N,N-dimethylformamide. The filtrate is concentrated under reduced pressure and filtered to afford the product (4.3 g), mp 283°-284° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. washrinsed with warm N,N-dimethylformamide
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. filtrationfiltered

Sources & evidence

ORD record
ord-48376c66ea3949c982275571ed8d9c8c
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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