[Cl:1][CH2:2][C:3]([N:5]([C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:17])[CH2:6][CH:7]=O)=[O:4].Cl.[NH2:19][OH:20].C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][CH2:2][C:3]([N:5]([C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:17])[CH2:6][CH:7]=[N:19][OH:20])=[O:4]A solution of 5 g (0.2 mol) alpha-(N-chloroacetyl-2-methyl-6-ethylphenylamino)acetaldehyde, 3.3 g (0.04 mol) hydroxylamine hydrochloride and 3.4 g (0.04 mol) sodium bicarbonate in 50 ml ethanol was heated at 40° C. for 40 minutes. The reaction mixture was filtered, evaporated under reduced pressure, diluted with ethyl ether, filtered again and evaporated under reduced pressure to give 5.5 g of a yellow oil which crystallized to a solid on standing. The crude solid was recrystallized from ethyl ether/hexane to give 3.2 g of the product as a white solid, m.p. 113°-115° C. The product is tabulated in Table I as Compound No. 11.
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