Pyridine → HCID 73886750, compound

HRID 1596147Notes

Reaction equation

HRID 1596147 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:8]2[CH:9]=[CH:10][C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[NH:21][OH:22])=[CH:12][C:7]=2[O:6][CH2:5]1.N1C=CC=CC=1.Cl[C:30]([O:32][CH3:33])=[O:31]>ClCCl>[CH3:1][O:2][N:3]=[C:4]1[C:8]2[CH:9]=[CH:10][C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:21]([OH:22])[C:30](=[O:31])[O:32][CH3:33])=[CH:12][C:7]=2[O:6][CH2:5]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 86757391HCID 86757391, compound

Product 1

HCID 73886750HCID 73886750, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.8 g of N-[2-(3-methoxyimino-2,3-dihydro-benzofuran-6-yloxymethyl)phenyl]-N-hydroxyamine and 1.3 g of pyridine in 50 ml of dichloromethane was cooled to 0° C. 1.4 g of methyl chloroformate was dropped into the solution. The temperature was slowly elevated to room temperature, and the reaction was further carried out for 8 hours. After the completion of the reaction, the reaction liquid was washed with a dilute aqueous hydrochloric acid solution and aqueous NaCl solution and then dried over anhydrous magnesium sulfate. After the concentration under reduced pressure, the obtained residue was dissolved in a mixed solution of 30 ml of methanol and 20 ml of tetrahydrofuran. 1.4 g of anhydrous potassium carbonate was added to the obtained solution, and they were stirred for 4 hours. Water and diethyl ether were added to the reaction solution, and the resultant mixture was neutralized with a dilute aqueous hydrochloric acid solution. After the extraction with diethyl ether, the extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue thus obtained was purified by the silica gel chromatography (hexane:ethyl acetate) to obtain 1.9 g of methyl N-[2-(3-methoxyimino-2,3-dihydrobenzofuran-6-yloxymethyl)phenyl]-N-hydroxycarbamate [1H-NMR (CDCl3) (ppm): 3.77 (3H, s), 3.93 (3H, s), 5.03 (2H, s), 5.13 (2H, s), 6.49-7.50 (m)].

Workup

  1. customwas slowly elevated to room temperature
  2. customAfter the completion of the reaction
  3. customthe reaction liquid
  4. washwas washed with a dilute aqueous hydrochloric acid solution and aqueous NaCl solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationAfter the concentration under reduced pressure
  7. dissolutionthe obtained residue was dissolved in a mixed solution of 30 ml of methanol and 20 ml of tetrahydrofuran
  8. addition1.4 g of anhydrous potassium carbonate was added to the obtained solution, and they
  9. additionWater and diethyl ether were added to the reaction solution
  10. extractionAfter the extraction with diethyl ether
  11. dry with materialthe extract was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue thus obtained
  14. customwas purified by the silica gel chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-c132c62db9d743a88ad0fd6a3545f0ee
Source dataset
uspto-grants-2001_09
Patent number
US06291399B1

Reaction notes

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