2-Chloro-6-methylaniline → 1-(6-Chloro-2-methyl-phenyl)amino-3-hydroxy-propane

HRID 1250890

Reaction equation

HRID 1250890 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][OH:14]>>[Cl:1][C:2]1[C:7]([NH:8][CH2:11][CH2:12][CH2:13][OH:14])=[C:6]([CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 68972-Chloro-6-methylanilineHCID 123083-Bromo-1-propanol

Product 1

HCID 183248341-(6-Chloro-2-methyl-phenyl)amino-3-hydroxy-propaneYield 77.5%

Conditions

Temperature
100 °C

Procedure

A mixture of the 6-chloro-2-methyl aniline (70.8 g) and 3-bromo-1-propanol (27.8 g) was heated under nitrogen to 100° C. for 2 hours. The mixture was cooled and partitioned between dichloromethane and 1N sodium hydroxide. The organic layer was washed with 20% aqueous sodium chloride, dried over anhydrous potassium carbonate and evaporated to dryness. The residue was flash chromatographed on Merck-60 flash silica gel. Elution with a hexane-ethyl acetate gradient (from 8:1 to 3:1) provided the title compound (30.86 g, 77.5%) as a pale yellow oil, which was used as such in the next step.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between dichloromethane and 1N sodium hydroxide
  3. washThe organic layer was washed with 20% aqueous sodium chloride
  4. dry with materialdried over anhydrous potassium carbonate
  5. customevaporated to dryness
  6. customchromatographed on Merck-60 flash silica gel
  7. washElution with a hexane-ethyl acetate gradient (from 8:1 to 3:1)

Sources & evidence

ORD record
ord-6933b08cc7444a80b7fc9aa0589b3d27
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Linked notes

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