2-Amino-5-methylpyridine → HCID 19610860, compound

HRID 1602206Notes

Reaction equation

HRID 1602206 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[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.ClCCl>[O:20]=[C:19]1[C:10]2[N:1]=[C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]3[C:11]=2[C:12](=[O:21])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]1=2

Participants

5

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 178516895HCID 178516895, compound

Product 1

HCID 19610860HCID 19610860, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

0.55 g (5.08 mmol) of 2-amino-5-methylpyridine is added to a suspension of 0.45 g (2.16 mmol) of 3-chloro-1,4-dihydro-1,4-dioxo-2-hydroxynaphthalene in 15 mL of 1,2-dimethoxyethane. The reaction medium is brought to reflux for 21 h. After complete cooling, it is diluted with 120 mL of dichloromethane. The organic phase is washed successively with a saturated solution of sodium hydrogen carbonate and sodium chloride, then dried on sodium sulfate and evaporated under reduced pressure. The raw product obtained is purified on a medium-pressure column (support: silica; eluent: dichloromethane/heptane/ethyl acetate, 68/40/2) to produce 0.096 g of 6,11-dihydro-6,11-dioxo-2-methyl-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 21 h
  2. washThe organic phase is washed successively with a saturated solution of sodium hydrogen carbonate and sodium chloride
  3. customdried on sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe raw product obtained
  6. customis purified on a medium-pressure column (support: silica; eluent: dichloromethane/heptane/ethyl acetate, 68/40/2)

Sources & evidence

ORD record
ord-f3503d1272f441f1991ded0d8631ebb9
Source dataset
uspto-grants-1999_11
Patent number
US05981544

Reaction notes

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