3-Chloro-4-methylaniline → HCID 18940892, compound

HRID 356014Notes

Reaction equation

HRID 356014 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].C(=O)([O-])O.[Na+].[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19]Br)[CH3:16]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:19][CH:18]([O:21][CH2:22][CH3:23])[O:17][CH2:15][CH3:16])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 72553-Chloro-4-methylanilineHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium Bicarbonate

Product 1

HCID 18940892HCID 18940892, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloro-4-methylaniline (10.26 g, 72.5 mmol), sodium hydrogen carbonate (9.1 g, 108 mmol) and bromoacetaldehyde diethyl acetal (13.1 ml, 87.1 mmol) were stirred at reflux under Ar in ethanol (150 ml) for 6 days. The mixture was then evaporated to dryness, partitioned between ether and water, and separated. The organic portion was washed with brine, dried (Na2SO4) and evaporated to a black oil. Bulb to bulb distillation of this crude material (oven temperature 175° C., ca 0.1 mmHg) then gave the title compound (4.90 g, 26%) as a colourless oil.

Workup

  1. customThe mixture was then evaporated to dryness
  2. custompartitioned between ether and water
  3. customseparated
  4. washThe organic portion was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to a black oil
  7. distillationBulb to bulb distillation of this crude material (oven temperature 175° C., ca 0.1 mmHg)

Sources & evidence

ORD record
ord-9719edf77fb045beb2bf1ed40375ea5c
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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