Hydrochloric Acid → HCID 54173222, compound

HRID 703211Notes

Reaction equation

HRID 703211 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][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].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>CO.C(OCC)(=O)C.O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][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

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86744460HCID 86744460, compound

Product 1

HCID 54173222HCID 54173222, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(2,3-dimethylphenyl)amino]benzaldehyde oxime (2.0 g, 8.4 mmol) and methyl orange (20 mg as an indicator), in methanol (40 ml) and water (10 ml) is added sodium cyanoborohydride (4.0 g, 64 mmol) in small portions over two hours, maintaining a red color of the indicator by the dropwise addition of concentrated HCl. The reaction of mixture is diluted with ethyl acetate (200 ml) and the aqueous layer is neutralized to pH=7 with 1N NaOH. The organic layer is collected, dried (MgSO4) and the solvent is evaporated to give crude 2-[(2,3-dimethylphenyl)amino]-N-hydroxy-benzenemethanamine as an oil which is used without further purification in the next step.

Workup

  1. temperaturemaintaining a red color of the indicator
  2. customThe reaction of mixture
  3. customThe organic layer is collected
  4. dry with materialdried (MgSO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-b3f9772c0bc54edb9eb92a5b5dde6aff
Source dataset
uspto-grants-1991_01
Patent number
US04981865

Reaction notes

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