Ammonia → HCID 15598837, compound

HRID 2292092Notes

Reaction equation

HRID 2292092 reaction equation
[CH:1]([CH:4]1[CH2:13][C:12](=[O:14])[NH:11][C:10]2[N:9]=[C:8](Br)[C:7]3[N:16]=[CH:17][CH:18]=[CH:19][C:6]=3[C:5]1=2)([CH3:3])[CH3:2].[C:20]([Cu])#[N:21].N>>[CH:1]([CH:4]1[CH2:13][C:12](=[O:14])[NH:11][C:10]2[N:9]=[C:8]([C:20]#[N:21])[C:7]3[N:16]=[CH:17][CH:18]=[CH:19][C:6]=3[C:5]1=2)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 15598819HCID 15598819, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 15598837HCID 15598837, compoundYield 21%

Procedure

1.6 g (0.005 mol) of 1-isopropyl-6-bromo-1,2-dihydropyrido[2,3-c][1,8]naphthyridin-3(4H)-one are melted at 220° C. in a heavy-oil bath with 0.45 g (0.05 mol) of CuCN. After 1 hour, the melt is cooled, and the residue is ground in a mortar and stirred with concentrated ammonia solution. The precipitate is filtered off under suction, washed with water, dried and purified on a silica gel column with chloroform. 0.28 g (21% of theory) of 1-isopropyl-6-cyano-1,2-dihydropyrido[2,3-c][1,8]naphthyridin-3(4H)-one is obtained.

Workup

  1. temperaturethe melt is cooled
  2. filtrationThe precipitate is filtered off under suction
  3. washwashed with water
  4. customdried
  5. custompurified on a silica gel column with chloroform

Sources & evidence

ORD record
ord-e5acdf53019942fe898c2b8948b2322f
Source dataset
uspto-grants-1989_01
Patent number
US04801590

Reaction notes

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