HCID 135525218, compound → N-methyl-2-(2-hydroxyphenyl)-2-methoxyiminoacetamide
Reaction equation
[CH3:1][NH:2][C:3](=[O:15])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])=[N:5]/[O:6][CH3:7].CNC(=O)/C(/C1C=CC=CC=1O)=N\OC>>[CH3:1][NH:2][C:3](=[O:15])[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])=[N:5][O:6][CH3:7]Participants
Procedure
4.33 g (0.0173 mol) of crude product methyl E/Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate, in particular Example II-1e from process step 8; HPLC: 27.4% methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=1.48 and 56% methyl Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=2.38) are dissolved in 50 ml of tetrahydrofuran and cooled to 10° C. With cooling, methylamine is introduced. After about 30 minutes, 15 ml of methanol are added, the solution is saturated with methylamine and the mixture is allowed to stand at 10° C. overnight. The solvents are distilled off under reduced pressure and the residue is mixed with a mixture of 15 ml of 2N hydrochloric acid and 15 ml of saturated sodium chloride solution and extracted three times with 25 ml of ethyl acetate each time. The organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure, giving 4.3 g of crude product which, according to HPLC, contains 38.8% N-methyl-E-2-(2-hydroxyphenyl)-2-methoxyimino-acetamide of log p=0.98 and 51% N-methyl-Z-2-(2-hydroxyphenyl)-2-methoxyiminoacetamide of log p=1.29.
Sources & evidence
- ORD record
- ord-4210eaeb23824db0a9bfaf8227665a2c
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06660872B1
Reaction notes
Loading…