Water → HCID 68603530, compound

HRID 2189153Notes

Reaction equation

HRID 2189153 reaction equation
[CH3:1][Li].[CH2:3]([O:7][C:8]1[CH:19]=[N:18][CH:17]=[CH:16][C:9]=1[C:10](N(OC)C)=[O:11])[CH:4]([CH3:6])[CH3:5].O>C1COCC1.Cl>[CH2:3]([O:7][C:8]1[CH:19]=[N:18][CH:17]=[CH:16][C:9]=1[C:10](=[O:11])[CH3:1])[CH:4]([CH3:5])[CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 86642356HCID 86642356, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 68603530HCID 68603530, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl lithium (4.6 mL, 7.4 mmol, 1.6M in Et2O, Aldrich) was added dropwise to a solution of 3-isobutoxy-N-methoxy-N-methylisonicotinamide (0.88 g, 3.7 mmol) in 15 mL of THF at 0° C. The reaction mixture was allowed to stir at 0° C. for an additional 1 h. To the resulting mixture were added 1 mL of water and 2 drops of conc HCl. The layers were separated and the aqueous layer was washed twice with 20 mL portions of Et2O. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The product was purified by SiO2 flash chromatography (50:50 hexanes/ethyl acetate) to 450 mg (63%) of the title compound. 1H-NMR (400 MHz, d6-DMSO): δ 8.54 (s, 1H), 8.27 (d, 1H), 7.41 (d, 1H), 4.01 (d, 2H), 2.55 (s, 3H), 2.06 (m, 1H), 0.99 (d, 6H). MS (EI) for C12H18N2O2: 194 (MH+).

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed twice with 20 mL portions of Et2O
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by SiO2 flash chromatography (50:50 hexanes/ethyl acetate) to 450 mg (63%) of the title compound

Sources & evidence

ORD record
ord-08a3c515148a497db965a2f58cf229b3
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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