Sodium Acetate → Hydrochloric Acid

HRID 428296Notes

Reaction equation

HRID 428296 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:22]=[CH:21][C:12]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=O)=[CH:11][CH:10]=1.[ClH:23].[CH3:24][O:25][NH2:26].C([O-])(=O)C.[Na+]>C(O)C>[CH3:24][O:25][N:26]=[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12]1[CH:21]=[CH:22][C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH2:1])=[CH:10][CH:11]=1.[ClH:23]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 11737779{4-[(2-Aminophenyl)amino]phenyl}(Phenyl)methanone2×

Product 2

HCID 313Hydrochloric AcidHCID 545068744-(2-Aminophenylamino)benzophenone O-methyloxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2-aminophenylamino)benzophenone (Compound 101. 0.29 g, 1mmol) and O-methylhydroxylamine hydrochloride (0.30 g, 3.5 mmol) in ethanol (10 ml) was added sodium acetate (0.30 g, 4 mmol). The reaction mixture was refluxed for 25 hours, cooled to room temperature, filtered, and evaporated in vacuo. The residue was treated with diluted ammonium hydroxide (10 ml) and extracted with ethyl acetate (2×25 ml). The organic phase was dried (MgSO4), filtered and evaporated in vacuo. The residue was dissolved in diethyl ether and acidified with hydrochloric acid in diethyl ether. The hydrochloride of the title compound instantaneously precipitate. The precipitate was triturated with ethyl acetate and washed with diethyl ether to yield the title compound as a hydrochloride.

Workup

  1. temperatureThe reaction mixture was refluxed for 25 hours
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. additionThe residue was treated with diluted ammonium hydroxide (10 ml)
  5. extractionextracted with ethyl acetate (2×25 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. dissolutionThe residue was dissolved in diethyl ether
  10. customThe precipitate was triturated with ethyl acetate
  11. washwashed with diethyl ether

Sources & evidence

ORD record
ord-4f0ac7c36906456a9337ed322c71f045
Source dataset
uspto-grants-2001_11
Patent number
US06313174B1

Reaction notes

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