Sodium Hydroxide → N-2-hydroxyethyl-3-chloro-4-fluoroaniline

HRID 896258Notes

Reaction equation

HRID 896258 reaction equation
C([O:3][C:4](=O)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([Cl:14])[CH:8]=1)C.[OH-].[Na+]>C1COCC1>[OH:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([Cl:14])[CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 302640Ethyl 2-(3-chloro-4-fluoroanilino)acetate

Product 1

HCID 22349678N-2-hydroxyethyl-3-chloro-4-fluoroanilineYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

ethyl-2-(3-chloro-4-fluoroanilino)acetate (J. Med. Chem. 1965, 405-407) (2 g, 8.6 mmol) in THF (15 ml) ether (10 ml) was treated with Li Al H4 (460 mg, 12.1 mmol) at 40° C. for 4 hours. The mixture was then poured onto ice, treated with NaOH (2N, 10 ml), extracted with ethyl acetate, dried, evaporated to give title compound (1.48 g, 90%).

Workup

  1. additionThe mixture was then poured onto ice
  2. extractionextracted with ethyl acetate
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-1b9e0d862d6c4498966e6517e4ffa6c8
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

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