Sodium Chloride → HCID 5131202, compound

HRID 1081880Notes

Reaction equation

HRID 1081880 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=O)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.[Cl-].[Na+]>C1COCC1>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]([CH:10]=1)[NH:4][CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 224170n-(5-chloro-2-nitrophenyl)acetamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 5131202HCID 5131202, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under ice cooling, the solution of N-acetyl-5-chloro-2-nitroaniline (3 g) in THF (30 ml) was added dropwise to the suspension of LiAlH4 (0.53 g) in THF (50 ml) over 30 minutes. The mixture was stirred under ice cooling for 1 hour. Into the resulting reaction solution was added ice with caution, followed by addition of ethyl acetate and saturated sodium chloride solution, and then insoluble materials was filtered off. The ethyl acetate layer was separated, washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the solvent, the residue was purified by chromatography on a silica gel column (hexane:ethyl acetate =19:1), to give the title compound (1.14 g; 41%).

Workup

  1. customInto the resulting reaction solution
  2. additionwas added ice with caution
  3. filtrationinsoluble materials was filtered off
  4. customThe ethyl acetate layer was separated
  5. washwashed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of the solvent
  8. customthe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate =19:1)

Sources & evidence

ORD record
ord-ebc2706b85684138b6f33aee9e74c56a
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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