4-Chloro-2-toluidine → N-(4-Chloro-2-methyl-phenyl)-propane-1,3-diamine

HRID 1250874Notes

Reaction equation

HRID 1250874 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.Br.Br[CH2:12][CH2:13][CH2:14][NH2:15].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:12][CH2:13][CH2:14][NH2:15])=[C:4]([CH3:9])[CH:3]=1

Participants

5

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-methylaniline (8 g) and 3-bromopropylamine hydrobromide (5 g) was heated at 100° C. for fifteen minutes. After cooling to room temperature, the resulting crystalline solid was dissolved in water (50 mL) and one equivalent of sodium hydroxide was added. This solution was then washed with ethyl ether and basified with excess sodium hydroxide. It was then extracted with dichloromethane, the combined extracts were dried over anhydrous potassium carbonate and evaporated to dryness.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThis solution was then washed with ethyl ether and basified with excess sodium hydroxide
  3. extractionIt was then extracted with dichloromethane
  4. dry with materialthe combined extracts were dried over anhydrous potassium carbonate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-d50cdada08774a14b9f3f62287fcc4b9
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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