Water → Ethyl hydroxyimino-[2-(2-methylaminoethyl)phenyl]acetate

HRID 2382153Notes

Reaction equation

HRID 2382153 reaction equation
COS([O-])(=O)=O.[CH2:7]([O:9][C:10]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][N+:13]=1[CH3:22])=[O:11])[CH3:8].[OH2:23].Cl.[NH2:25]O.[OH-].[Na+]>C(OCC)(=O)C>[OH:23][N:25]=[C:12]([C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:15][CH2:14][NH:13][CH3:22])[C:10]([O:9][CH2:7][CH3:8])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 250225581-Ethoxycarbonyl-3,4-dihydro-2-methylisoquinolinium monomethylsulfate

Product 1

HCID 73012975Ethyl hydroxyimino-[2-(2-methylaminoethyl)phenyl]acetateYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The 1-ethoxycarbonyl-3,4-dihydro-2-methylisoquinolinium monomethylsulfate solution obtained by Reference Example A4 was added with 60 ml of water and 22.4 g (322 mmol) of hydroxylamine hydrochloride in a flask. The mixture was stirred at room temperature for six hours. The reaction mixture was added with 120 ml of ethyl acetate, and then the pH was adjusted at 9 to 10 with about 103 g of aqueous sodium hydroxide solution (25%) to yield precipitation. The solution was stirred at 5° C. for 30 minutes. Then, the precipitation was filtered, washed with ethyl acetate, and dried to obtain 42.2 g (169 mmol, yield 55%, 3 steps) of ethyl hydroxyimino-[2-(2-methylaminoethyl)phenyl]acetate as white crystals.

Workup

  1. customto yield
  2. customprecipitation
  3. stirringThe solution was stirred at 5° C. for 30 minutes
  4. customThen, the precipitation
  5. filtrationwas filtered
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-65a07a2480794a4db6027ec41f89ad53
Source dataset
uspto-grants-2012_09
Patent number
US08258302B2

Reaction notes

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