Acetic Anhydride → Methyl 3-(4-{5-[amino(imino)methyl]pyridin-2-yl}phenoxy)-2,2-dimethylpropanoate acetate

HRID 623933Notes

Reaction equation

HRID 623933 reaction equation
[NH2:1][C:2](=[N:24]O)[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:23]=[CH:22][C:12]([O:13][CH2:14][C:15]([CH3:21])([CH3:20])[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.C(OC(=O)C)(=O)C>C(O)(=O)C>[C:16]([OH:18])(=[O:17])[CH3:15].[NH2:24][C:2](=[NH:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]([CH3:20])([CH3:21])[C:16]([O:18][CH3:19])=[O:17])=[CH:22][CH:23]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86698185Methyl 3-(4-{5-[amino(hydroxyimino)methyl]pyridin-2-yl}phenoxy)-2,2-dimethylpropanoate

Product 1

HCID 67973181Methyl 3-(4-{5-[amino(imino)methyl]pyridin-2-yl}phenoxy)-2,2-dimethylpropanoate acetateYield 186.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In acetic acid (60 mL) was dissolved methyl 3-(4-{5-[amino(hydroxyimino)methyl]-pyridin-2-yl}phenoxy)-2,2-dimethylpropanoate (5.8 g), acetic anhydride (4 mL) was added to the solution and the mixture was stirred at room temperature for 2 hours. To the residue obtained by concentrating the mixture under reduced pressure were added methanol (300 mL) and tetrahydrofuran (70 mL), and 10% palladium carbon (1.2 g) was added to the mixture under nitrogen atmosphere. The atmosphere of the reaction mixture was made hydrogen atmosphere, and the mixture was stirred at room temperature for 2 hours. After replacing the atmosphere with nitrogen, the mixture was filtered using Celite. The filtrate was concentrated under reduced pressure, ether was added to the obtained residue to pulverize the solid, and the solid was collected by filtration and dried to obtain methyl 3-(4-{5-[amino(imino)methyl]pyridin-2-yl}-phenoxy)-2,2-dimethylpropanoate acetate (6.11 g).

Workup

  1. additionwas added to the solution
  2. customTo the residue obtained
  3. concentrationby concentrating the mixture under reduced pressure
  4. additionwere added methanol (300 mL) and tetrahydrofuran (70 mL), and 10% palladium carbon (1.2 g)
  5. additionwas added to the mixture under nitrogen atmosphere
  6. stirringthe mixture was stirred at room temperature for 2 hours
  7. filtrationthe mixture was filtered
  8. concentrationThe filtrate was concentrated under reduced pressure, ether
  9. additionwas added to the obtained residue
  10. filtrationthe solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-1370beae6c93478b8de214bfee5764a0
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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