Methanol → (E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide

HRID 376039

Reaction equation

HRID 376039 reaction equation
C[O:2][C:3](=O)/[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:5]/[OH:6].CO.[CH3:23][NH2:24].O>C1(C)C=CC=CC=1>[OH:6]/[N:5]=[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:3]([NH:24][CH3:23])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6329Methylamine2×HCID 88276687methyl (2E)-2-hydroxyimino-2-(2-phenoxyphenyl)acetate

Product 1

HCID 9816878(E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamideYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To crude E-a-hydroxyimino-2-phenoxyphenylacetic acid methyl ester (39.6 g, 0.0747 mole, purity: 51.2%) were added methanol (100 ml) and 40% aqueous solution of methylamine (15.45 g, 0.199 mole) and the mixture was stirred at room temperature for 15 hours. Then, 40% aqueous solution of methylamine (7.73 g, 0.0995 mole) was added to the mixture which was stirred in an oil bath at 70° C. for 6 hours. After completion of the reaction, water (200 ml) and toluene (100 ml) were added to the reaction mixture, which was stirred with ice cooling for one hour. The precipitated crystals were filtered off and recrystallized (methanol/toluene) to obtain E-2-hydroxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide (12.31 g, yield: 60.1%) as colorless crystals (melting point: 183°-184.5° C.).

Workup

  1. stirringwas stirred in an oil bath at 70° C. for 6 hours
  2. additionwere added to the reaction mixture, which
  3. stirringwas stirred with ice cooling for one hour
  4. filtrationThe precipitated crystals were filtered off
  5. customrecrystallized (methanol/toluene)

Sources & evidence

ORD record
ord-96ca491ac0e4457f970b189090d63d42
Source dataset
uspto-grants-1996_01
Patent number
US05488159

Linked notes

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