Hydrochloric Acid → Desmethylamino Methoxy (E)-Metominostrobin

HRID 2081291Notes

Reaction equation

HRID 2081291 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](\[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)/[C:5]#N.Cl.[C:21](=O)(O)[O-:22].[Na+].C[OH:27]>>[CH3:21][O:22][C:5](=[O:27])/[C:4](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:3]/[O:2][CH3:1]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 11128775(1E)-N-methoxy-2-phenoxybenzenecarboximidoyl cyanide

Product 1

HCID 10803045Desmethylamino Methoxy (E)-MetominostrobinYield 46.7%

Procedure

To E-α-methoxyimino-2-phenoxyphenylacetonitrile (a mixture of E- and Z-isomers) (0.76 g, 0.003 mole) was added 30% hydrochloric acid in methanol (4.5 ml) and the mixture was stirred under reflux for 22 hours. After completion of the reaction, 8% aqueous solution of sodium bicarbonate (100 ml) was added to the reaction mixture and extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain E-α-methoxyimino-2-phenoxyphenylacetic acid methyl ester (0.40 g, 46.7%) as colorless crystals (melting point: 109°-110° C.).

Workup

  1. temperatureunder reflux for 22 hours
  2. additionwas added to the reaction mixture
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-1c90244f02ed4ea286086740f49ea6fb
Source dataset
uspto-grants-1993_02
Patent number
US05183921

Reaction notes

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