5-Chloro-2-methylaniline → HCID 18324843, compound

HRID 1250883Notes

Reaction equation

HRID 1250883 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].Br[CH2:11][CH2:12][CH2:13][OH:14]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([NH:7][CH2:11][CH2:12][CH2:13][OH:14])[CH:8]=1

Participants

4

Reactant 2

HCID 72605-Chloro-2-methylanilineHCID 123083-Bromo-1-propanol

Product 1

HCID 18324843HCID 18324843, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-2-methylaniline (10.1 g) and 3-bromo-1-propanol (2.5 mL) were heated at 100° C. under nitrogen for 45 minutes. After cooling, a solid mass formed which was partitioned between dichloromethane and 1N sodium hydroxide. The organic phase 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 20% ethyl acetate in hexane gave the title compound (5.6 g, 98.1%) 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 phase 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 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e8be8f1e2f164cddbee6495871ced755
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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