4-Chloro-2-toluidine → 3-(2-Methyl-4-chloroanilino)propionaldehyde

HRID 1576940Notes

Reaction equation

HRID 1576940 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Br[CH:11]([CH3:14])[CH:12]=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][CH2:14][CH2:11][CH:12]=[O:13]

Participants

4

Reactant 3

HCID 72514-Chloro-2-toluidineHCID 10340Sodium CarbonateHCID 3506242-Bromopropanal

Product 1

HCID 215102843-(2-Methyl-4-chloroanilino)propionaldehyde

Conditions

Temperature
150 °C

Procedure

2-Methyl-4-chloroaniline (1.0 mole), the diethyl acetal of 2-bromopropionaldehyde (1.0 mole) and sodium carbonate (1.0 mole) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The mixture is heated at a temperature of about 150°C for a period of about 24 hours. After this time the reaction mixture is cooled to room temperature and is filtered. The filtrate is then distilled under vacuum to yield the desired product the diethyl acetal of 3-(2-methyl-4-chloroanilino)propionaldehyde as the residue.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureAfter this time the reaction mixture is cooled to room temperature
  4. filtrationis filtered
  5. distillationThe filtrate is then distilled under vacuum

Sources & evidence

ORD record
ord-f33261b76033415585048cf73267c0af
Source dataset
uspto-grants-1976_09
Patent number
US03983174

Reaction notes

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