2-Amino-5-chloropyridine → HCID 19610867, compound

HRID 1602207Notes

Reaction equation

HRID 1602207 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:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:21])[C:11]=1O>COCCOC.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:11]3[C:12](=[O:21])[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19](=[O:20])[C:10]=3[N:1]=2)[CH:4]=1

Participants

5

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 178516895HCID 178516895, compound

Product 1

HCID 19610867HCID 19610867, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.58 g (12.30 mmol) of 2-amino-5-chloropyridine are added to a suspension of 1.29 g (6.21 mmol) of 3-chloro-1,4-dihydro-1,4-dioxo-2-hydroxynaphthalene in solution in 10 mL of 1,2-dimethoxyethane. The reaction medium is brought to reflux for 23 h. After complete cooling, the medium is diluted in 10 mL of water. The precipitate is filtered, washed with water and heptane, and dried. The precipitate is then diluted in dichloromethane and the organic phase is washed successively with a saturated solution of sodium hydrogen carbonate and sodium chloride. The organic phase is dried on sodium sulfate, filtered, and evaporated under reduced pressure. The raw product obtained is purified on a flash column (support: silica; eluent: dichoromethane/heptane/methanol, 79.5/20.0/0.5) to produce 0.07 g of 2-chloro-6,11-dihydro-6,11-dioxo-naphtho[2',3':4,5]imidazo [1,2-a]pyridine in the form of yellow crystals after decoloration with animal black.

Workup

  1. temperatureto reflux for 23 h
  2. filtrationThe precipitate is filtered
  3. washwashed with water and heptane
  4. customdried
  5. additionThe precipitate is then diluted in dichloromethane
  6. washthe organic phase is washed successively with a saturated solution of sodium hydrogen carbonate and sodium chloride
  7. customThe organic phase is dried on sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe raw product obtained
  11. customis purified on a flash column (support: silica; eluent: dichoromethane/heptane/methanol, 79.5/20.0/0.5)

Sources & evidence

ORD record
ord-b2e9060099ed49ed9a18291d78f226bf
Source dataset
uspto-grants-1999_11
Patent number
US05981544

Reaction notes

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