1,2,3,4-Tetrahydro-8-methoxy-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one → 9-Amino-1,2,3,4-tetrahydro-8-methoxy-3-(2-oxopropyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 851199Notes

Reaction equation

HRID 851199 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]2[C:12]3[CH2:17][CH2:16][NH:15][CH2:14][C:13]=3[C:18](=[O:20])[O:19][C:5]=2[CH:4]=1>CN(C)C=O.[Ni]>[NH2:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[O:19][C:18](=[O:20])[C:13]3[CH2:14][N:15]([CH2:4][C:3](=[O:2])[CH3:8])[CH2:16][CH2:17][C:12]=3[C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 131369251,2,3,4-Tetrahydro-8-methoxy-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one

Product 1

HCID 131369429-Amino-1,2,3,4-tetrahydro-8-methoxy-3-(2-oxopropyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-oneYield 115.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

1,2,3,4-Tetrahydro-8-methoxy-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one (13.0 g) in N,N-dimethylformamide (130 ml) is hydrogenated over Raney Nickel (2 g). The Raney Nickel is filtered off. The solvent is evaporated to give a light brown solid. The solid is triturated with methanol, washed with methanol, and dried to give the product (8.2 g), mp 178°-180° C.

Workup

  1. filtrationThe Raney Nickel is filtered off
  2. customThe solvent is evaporated
  3. customto give a light brown solid
  4. customThe solid is triturated with methanol
  5. washwashed with methanol
  6. customdried

Sources & evidence

ORD record
ord-a1659433546442d787607089321ab8dd
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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