2-Amino-5-chloropyridine → HCID 15410611, compound

HRID 1602205Notes

Reaction equation

HRID 1602205 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.Cl[C:10]1[C:11](=[O:25])[C:12]2[C:17]([C:18](=[O:21])[C:19]=1Cl)=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=[CH:14][CH:13]=2>C(O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:10]3[C:11](=[O:25])[C:12]4[CH:13]=[CH:14][CH:15]=[C:16]([N+:22]([O-:24])=[O:23])[C:17]=4[C:18](=[O:21])[C:19]=3[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 43814362,3-Dichloro-5-nitro-1,4-naphthoquinone

Product 1

HCID 15410611HCID 15410611, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.50 g (19.0 mmol) of 2-amino-5-chloropyridine are added to a solution of 2.50 g (11.0 mmol) of 2,3-dichloro-1,4-dihydro-1,4-dioxo-5-nitronaphthalene in 500 mL of ethanol. This mixture is heated to reflux for 62 h and 50 min. The solution passes from yellow to claret-colored, then to orange. After cooling, the reaction mixture is filtered. The precipitate is washed with ethanol, then dried in an oven for 20 h. The precipitate obtained is recrystallized in 650 mL of ethanol. This precipitate is purified on a flash column (support: silica; eluent: dichloromethane). 0.260 g of 2-chloro-6,11-dihydro-6,11-dioxo-7-nitronaphtho[2',3':4,5]imidazo[1,2-a]-pyridine or 2-chloro-6,11-dihydro-6,11-dioxo-10-nitronaphtho[2',3':4,5]imidazo[1,2-a] pyridine is obtained in the form of orange crystals, and 0.495 g of 10-chloro-5,6-dihydro-5,6-dioxo-4-nitronaphtho[1',2':4,5] imidazo[1,2-a]pyridine is formed in the form of orange crystals.

Workup

  1. temperatureThis mixture is heated
  2. temperatureto reflux for 62 h and 50 min
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered
  5. washThe precipitate is washed with ethanol
  6. customdried in an oven for 20 h
  7. customThe precipitate obtained
  8. customis recrystallized in 650 mL of ethanol
  9. customThis precipitate is purified on a flash column (support: silica; eluent: dichloromethane)

Sources & evidence

ORD record
ord-f6d91aaf88d54cfdb59a29005ec125a9
Source dataset
uspto-grants-1999_11
Patent number
US05981544

Reaction notes

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