Triethylamine → HCID 86754302, compound

HRID 583145Notes

Reaction equation

HRID 583145 reaction equation
[C:1]([NH:4][C:5]1[C:14](C=O)=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[Cl:17])(=[O:3])[CH3:2].Cl.[O:19]([NH2:21])[CH3:20].[CH2:22](N(CC)CC)C>C(Cl)Cl>[C:1]([NH:4][CH:5]1[C:14](=[N:21][O:19][CH3:20])[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([CH3:22])=[C:6]1[Cl:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 17760218HCID 17760218, compound

Product 1

HCID 86754302HCID 86754302, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (ice bath) of 2.6 g (10.15 mmole) of methyl 4-acetamido-3-chloro-5-formylbenzoate in 75 ml of methylene chloride was added 1.16 g (13.87 mmole) of methoxylamine hydrochloride followed by 1.93 mL (13.87 mmole) of triethylamine. The ice bath was removed and the resulting mixture stirred overnight at room temperature. The reaction mixture was then washed with water and dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator, yielding 2.29 g methyl 4-acetamido-3-chloro-5-methoxyimino-methylbenzoate used without further purification in the next step.

Workup

  1. customThe ice bath was removed
  2. washThe reaction mixture was then washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-9238ea1b631e4f53a69ec5f552204d9b
Source dataset
uspto-grants-1999_07
Patent number
US05929098

Reaction notes

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