4-Chloro-2-toluidine → HCID 18324828, compound

HRID 1250888Notes

Reaction equation

HRID 1250888 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.Br[CH2:11][CH2:12][CH2:13][OH:14]>ClCCl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:11][CH2:12][CH2:13][OH:14])=[C:4]([CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 72514-Chloro-2-toluidineHCID 123083-Bromo-1-propanol

Product 1

HCID 18324828HCID 18324828, compoundYield 143.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-methylaniline (35.7 g) and 3-bromo-1-propanol (8.75 g) was heated at 100° C. under nitrogen for 1 hour. After cooling, a solid mass formed which was partitioned between dichloromethane and 1N sodium hydroxide. The organic layer was washed with brine, dried over anhydrous potassium carbonate and concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with a solvent gradient (from 100% dichloromethane to 95:5 dichloromethane-methanol) provided the title product (18.0 g, 90%) as a brown oil, which was used as such in the next step.

Workup

  1. temperatureAfter cooling
  2. customa solid mass formed which
  3. customwas partitioned between dichloromethane and 1N sodium hydroxide
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous potassium carbonate
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil
  8. customabsorbed onto a column of Merck-60 flash silica gel
  9. washElution with a solvent gradient (from 100% dichloromethane to 95:5 dichloromethane-methanol)

Sources & evidence

ORD record
ord-2231a66b292848399ebe8d012ecd9dd8
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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