Methanol → HCID 68525839, compound

HRID 1932538Notes

Reaction equation

HRID 1932538 reaction equation
Cl.[NH2:2]O.C(=O)([O-])[O-].[Na+].[Na+].C[O:11][C:12](=O)[C:13](=[CH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:42])[C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=3)=[CH:28][N:27]=2)=[CH:21][CH:20]=1)[C:14]([O:16]C)=[O:15].CO>O.C1COCC1>[Cl:41][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][C:37]=1[Cl:40])[C:33]([NH:32][C:29]1[CH:28]=[N:27][C:26]([O:25][C:22]2[CH:21]=[CH:20][C:19]([CH:18]=[C:13]3[C:14](=[O:15])[O:16][NH:2][C:12]3=[O:11])=[CH:24][CH:23]=2)=[CH:31][CH:30]=1)=[O:42]

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 68527081HCID 68527081, compound

Product 1

HCID 68525839HCID 68525839, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of hydroxylamine hydrochloride (500 mg, 1.0 mmol) in water (0.2 mL) were added sodium carbonate (1.05 g, 9.91 mmol) and a solution of 2-{4-[5-(3,4-dichlorobenzoylamino)pyridin-2-yloxy]benzylidene}malonic acid dimethyl ester (500 mg, 1.0 mmol) in THF (5 mL). To the resulting solution was subsequently added methanol (5 mL) and stirred for 8 hours at 60° C. The reaction solution was concentrated under reduced pressure. Water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1). To the resulting white precipitate was added ethyl acetate, filtered, and the filtrate was washed with diethyl ether, to thereby yield 105 mg of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1)
  8. additionTo the resulting white precipitate was added ethyl acetate
  9. filtrationfiltered
  10. washthe filtrate was washed with diethyl ether

Sources & evidence

ORD record
ord-ed9eab63109c4ee2a9658c80de5c5a18
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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