HCID 13136936, compound → HCID 13136941, compound

HRID 851208Notes

Reaction equation

HRID 851208 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][N:14]([CH2:17][C:18](=[O:20])[CH3:19])[CH2:13][C:12]=3[C:21](=[O:23])[O:22][C:4]=2[CH:3]=1.[H][H]>CN(C)C=O.[Ni]>[NH2:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]2[O:22][C:21](=[O:23])[C:12]3[CH2:13][N:14]([CH2:17][C:18](=[O:20])[CH3:19])[CH2:15][CH2:16][C:11]=3[C:5]=2[CH:6]=1

Participants

5

Reactant 2

HCID 13136936HCID 13136936, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13136941HCID 13136941, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,2,3,4-tetrahydro-8-methyl-9-nitro-3-(2-oxopropyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one (17.2 g, 0.054 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 (10.9 g), mp 196°-198° 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

Sources & evidence

ORD record
ord-e4ff718c7568417ba3def6b2f4e42c6e
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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