Methylamine → 4-chloro-2-(hydroxymethyl)-N-methylbenzamide

HRID 2252817Notes

Reaction equation

HRID 2252817 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[CH:13]=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1>CO>[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([NH:2][CH3:1])=[O:11])=[C:6]([CH2:10][OH:9])[CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 2417375-Chloro-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 691802354-chloro-2-(hydroxymethyl)-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methylamine gas was condensed into a sealed tube at −78° C., and a solution of 5-chloro-2-benzofuran-1(3H)-one (6.68 g, 39.8 mmol) in methanol (30 mL) was added. The solution was slowly warmed to room temperature overnight; The reaction was concentrated in vacuo, and the residue was partitioned between water and and chloroform. After three extractions with chloroform, the combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 4-chloro-2-(hydroxymethyl)-N-methylbenzamide.

Workup

  1. customcondensed into a sealed tube at −78° C.
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was partitioned between water and and chloroform
  4. extractionAfter three extractions with chloroform
  5. dry with materialthe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55e528e2c8444b6191108304948f3a54
Source dataset
uspto-grants-2008_01
Patent number
US07323460B2

Reaction notes

Loading…