o-Chlorophenylacetic acid → HCID 46318635, compound

HRID 2354097Notes

Reaction equation

HRID 2354097 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([OH:16])=O>ClCCl>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([N:3]([O:4][CH3:5])[CH3:2])=[O:16]

Participants

4

Reactant 2

HCID 17124o-Chlorophenylacetic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 46318635HCID 46318635, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

Under ice-cooling, N,O-dimethylhydroxylamine hydrochloride (3.42 g) was added to a mixture of (2-chlorophenyl)acetic acid (3.41 g) and WSCD (2.05 g) in dichloromethane (30 mL). The mixture was stirred at 0-10° C. for an hour and at 20-25° C. for 20 hours, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was purified by silica gel (chromatorex NH) (hexane-AcOEt 50:50 v/v) to give 2-(2-chlorophenyl)-N-methoxy-N-methylacetamide as oil (3.99 g).

Workup

  1. temperatureUnder ice-cooling
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue
  6. customThe residue was purified by silica gel (chromatorex NH) (hexane-AcOEt 50:50 v/v)

Sources & evidence

ORD record
ord-17cb3c9219fd4b9da5b47c6816594ab6
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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