Hydrochloric Acid → HCID 57867419, compound

HRID 1894692Notes

Reaction equation

HRID 1894692 reaction equation
[C:1]([C:4]1[C:5]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[C:17](OCC)(=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19].CC(C)([O-])C.[K+].Cl.Cl.[NH2:35]O.[OH-].[Na+]>C1(C)C=CC=CC=1.O.C(O)C>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([NH:10][C:5]1[C:4]([C:1]2[O:3][N:35]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:2]=2)=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:16]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19354338HCID 19354338, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 57867419HCID 57867419, compoundYield 59.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
-25 °C

Procedure

To a mixture of N-(3-acetyl pyridin-2-yl)-2,2-dimethylpropanamide (8.08 g, 36.7 mmol), diethyl oxalate (10.0 mL, 73.4 mmol) and ethanol (36 mL) was added potassium tert-butoxide (8.23 g, 73.4 mmol) at −25° C., which was stirred at −25° C. for one hour. The reaction mixture was added water (72 mL), which was stirred at room temperature, toluene (36 mL) was added, separated, and the obtained aqueous layer was further washed with toluene (36 mL). To the solution were added 5N hydrochloric acid (14 mL) and hydroxylamine hydrochloride (5.10 g, 73.4 mmol), which was stirred at room temperature for 30 minutes. To the reaction mixture was added 5N aqueous sodium hydroxide (14 mL), which was extracted with toluene, the solvent was evaporated under a reduced pressure. To the obtained residue were added ethanol (35 mL) and triethylamine (5 mL), which was stirred at 80° C. to 85° C. for six hours. To the reaction mixture was added n-heptane (105 mL) and the precipitated solid was filtered to obtain the title compound (6.90 g).

Workup

  1. stirringwas stirred at room temperature
  2. customseparated
  3. washthe obtained aqueous layer was further washed with toluene (36 mL)
  4. stirringwas stirred at room temperature for 30 minutes
  5. extractionwas extracted with toluene
  6. customthe solvent was evaporated under a reduced pressure
  7. additionTo the obtained residue were added ethanol (35 mL) and triethylamine (5 mL), which
  8. stirringwas stirred at 80° C. to 85° C. for six hours
  9. additionTo the reaction mixture was added n-heptane (105 mL)
  10. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-3a37eb4d120f477fb3175715c070d5c6
Source dataset
uspto-grants-2013_08
Patent number
US08513287B2

Reaction notes

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