Ammonia → HCID 59138781, compound

HRID 1751960Notes

Reaction equation

HRID 1751960 reaction equation
C[N:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[C:3]1=O.[O:15]1[C:19]2([CH2:24]CC(=O)[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1.N>CO>[N+:8]([C:6]1[CH:7]=[N:2][C:3]2[CH2:21][CH2:20][C:19]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:24][C:4]=2[CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 59138781HCID 59138781, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The title compound was prepared according to the procedure of Takada (J. Med. Chem. 1996, 39, 2844-2851). A 350 mL pressure vessel, equipped with a magnetic stir bar, was charged with 1-methyl-3,5-dinitropyridin-2(1H)-one (5.0 g, 25.1 mmol) and 1,4-dioxaspiro[4.5]decan-8-one (4.7 g, 30.1 mmol). Ammonia in MeOH (1M, 200 mL) was added, the vessel was sealed with a screw cap, and the mixture was heated to 60° C. and stirred for 17 hours. The reaction mixture was concentrated and the residue was partitioned with ethyl acetate (200 mL) and water (200 mL). The layers were separated and the aqueous portion was extracted with ethyl acetate (2×100 mL). The organic portions were combined, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (7/3, hexanes/ethyl acetate) to afford the title compound (4.85 g, 82%).

Workup

  1. customThe title compound was prepared
  2. customA 350 mL pressure vessel, equipped with a magnetic stir bar
  3. customthe vessel was sealed with a screw
  4. customcap
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was partitioned with ethyl acetate (200 mL) and water (200 mL)
  7. customThe layers were separated
  8. extractionthe aqueous portion was extracted with ethyl acetate (2×100 mL)
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel chromatography (7/3, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-594a2929843e4bab819b9b2aed759e75
Source dataset
uspto-grants-2015_10
Patent number
US09162983B2

Reaction notes

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