Ammonia → HCID 59295674, compound

HRID 252905Notes

Reaction equation

HRID 252905 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][O:6][C:5]2([CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9][CH2:8]2)[O:4][CH2:3]1.C[N:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=C([N+]([O-])=O)C1=O.N>CO>[CH3:1][C:2]1([CH3:16])[CH2:7][O:6][C:5]2([CH2:14][CH2:13][CH2:12][C:11]3=[N:18][CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[C:10]3[CH2:9][CH2:8]2)[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-oneHCID 59295611HCID 59295611, compound

Product 1

HCID 59295674HCID 59295674, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3,3-dimethyl-1,5-dioxaspiro[5.7]tridecan-10-one (compound of formula (Ca)) (1.32 g, 5.83 mmol), 1-methyl-3,5-dinitro-1H-pyridin-2-one (compound of formula (Cb)) (1.07 g, 5.3 mmol) and 7N ammonia solution in methanol (45 mL) was heated at 80° C. in sealed vessel overnight. The solvent was evaporated and the residue was dissolved in dichloromethane (DCM). The soluble portion was concentrated and purified by flash chromatography on silica gel (hexane/ethyl acetate, 3:1) to give the compound of formula (Cc), 5′,5′-dimethyl-3-nitro-6,8,9,10-tetrahydro-5H-spiro[cycloocta[b]pyridine-7,2′-[1,3]dioxane] (1.5 g, 92.5%); 1H NMR (DMSO-d6, 300 MHz) 9.09 (s, 1H), 8.40 (s, 1H), 3.37 (m, 4H), 3.02 (t, 2H), 2.89 (m, 2H), 2.02 (m, 2H), 1.77 (m, 2H), 1.58 (t, 2H), 0.86 (d, 6H) ppm; MS (ES) 306.99 (M+H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane (DCM)
  3. concentrationThe soluble portion was concentrated
  4. custompurified by flash chromatography on silica gel (hexane/ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-96a6bf0e60c14c108df3daf26ff0aac0
Source dataset
uspto-grants-2011_01
Patent number
US07872000B2

Reaction notes

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