Sodium Hydroxide → HCID 54266560, compound

HRID 1461430Notes

Reaction equation

HRID 1461430 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[CH:12]=[N:13][OH:14].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[CH2:12][NH:13][OH:14]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86744461HCID 86744461, compound

Product 1

HCID 54266560HCID 54266560, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(2,6-dichlorophenyl)amino]benzaldehyde oxime (4.0 g, 13.6 mmol) in glacial acetic acid (20 ml) is added sodium cyanoborohydride (2.05 g,33 mmol) in small portions over a period of two hours. The reaction mixture is diluted with ethyl acetate (200 ml) and neutralized with lN NaOH. The organic layer is collected and the solvent is evaporated. 2-[(2,6-Dichlorophenyl)amino]-N-hydroxybenzenemethanamine (3.5 g, 91%) is isolated as an oil by flash chromatography (silica, 3:1 chloroformethyl acetate). The compound is not further purified, but used directly in the next reaction.

Workup

  1. customThe organic layer is collected
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-89ca49e46d93432986120e1cc3f8a116
Source dataset
uspto-grants-1991_12
Patent number
US05075330

Reaction notes

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