Potassium Sodium Tartrate → 3-chloro-N-ethyl-4-fluoroaniline

HRID 1974616Notes

Reaction equation

HRID 1974616 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[F:18])[NH:11][C:12](=O)[CH3:13].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CCOCC.C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[F:18])[NH:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 589188N-(3-Chloro-4-fluorophenyl)acetamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 142024823-chloro-N-ethyl-4-fluoroanilineYield 97.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of lithium aluminium hydride (44.1 g, 1.16 mmol) in absolute ether (700 ml) is treated dropwise with a solution of 3'-chloro-4'-fluoroacetanilide (BE Patent No. 891537; 109 g, 0.576 mol) in absolute THF (350 ml). The suspension obtained is stirred for 2 hours, then cooled to 0° and treated with a Rochelle salt solution (350 ml). The crystals obtained are filtered off and washed with ether. The organic solution is dried over magnesium sulphate and the solvent is distilled off under reduced pressure. There are obtained 97.5 g (97.5%) of 3-chloro-N-ethyl-4-fluoroaniline as an amorphous material.

Workup

  1. customThe suspension obtained
  2. temperaturecooled to 0°
  3. customThe crystals obtained
  4. filtrationare filtered off
  5. washwashed with ether
  6. dry with materialThe organic solution is dried over magnesium sulphate
  7. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-d75e15cedc8e4c92835accc47f92c250
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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