Hydroxylamine → Methyl 3-(4-{5-[amino(hydroxyimino)methyl]pyridin-2-yl}phenoxy)-2,2-dimethylpropanoate

HRID 623932Notes

Reaction equation

HRID 623932 reaction equation
[NH2:1][OH:2].CO.[C:5]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=2)=[N:11][CH:12]=1)#[N:6]>O1CCCC1>[NH2:6][C:5](=[N:1][OH:2])[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 887MethanolHCID 67973192Methyl 3-[4-(5-cyanopyridin-2-yl)-phenoxy]-2,2-dimethylpropanoate

Product 1

HCID 86698185Methyl 3-(4-{5-[amino(hydroxyimino)methyl]pyridin-2-yl}phenoxy)-2,2-dimethylpropanoateYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

50% Aqueous hydroxylamine solution (40 g) was added to a methanol (100 mL) and tetrahydrofuran (100 mL) solution containing methyl 3-[4-(5-cyanopyridin-2-yl)-phenoxy]-2,2-dimethylpropanoate (6.0 g), and the mixture was stirred at 80° C. for 4 hours. After cooling the reaction mixture to room temperature, the mixture was concentrated under reduced pressure. To the obtained residue were added ethyl acetate and water, and the liquids were separated. The organic layer was separated, washed with water, and dried over anhydrous sodium sulfate. Ether was added to the solid residue obtained by concentrating the mixture under reduced pressure to pulverize the same, and the solid was collected by filtration and dried to obtain methyl 3-(4-{5-[amino(hydroxyimino)methyl]pyridin-2-yl}phenoxy)-2,2-dimethylpropanoate (5.8 g).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionTo the obtained residue were added ethyl acetate and water
  4. customthe liquids were separated
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. additionEther was added to the solid residue
  9. customobtained
  10. concentrationby concentrating the mixture under reduced pressure
  11. filtrationwas collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-aeb11c8cd2da4f668149bca2c8a08711
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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