Sodium Hydroxide → Benzophenone, 2,5-diamino-2'-chloro-

HRID 358048Notes

Reaction equation

HRID 358048 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:5].[Sn](Cl)Cl.[OH-].[Na+]>Cl>[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 748302-Amino-5-nitro-2'-chlorobenzophenone

Product 1

HCID 521842Benzophenone, 2,5-diamino-2'-chloro-

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

100 g of 2-amino-2'-chloro-5-nitrobenzophenone are suspended in 865 ml of 25% hydrochloric acid and treated portionwise with a total of 269 g of tin (II) chloride. The mixture is stirred at room temperature for 36 hours, then diluted with 0.5 l of an ice/water mixture and adjusted to pH 10 with about 2.17 l of a 28% sodium hydroxide solution. The mixture is extracted with methylene chloride. After evaporation of the solvent, the residue is dissolved in 0.54 l of ether and crystallized at about -20°. There is obtained 2,5-diamino-2'-chlorobenzophenone of melting point 30°-40°.

Workup

  1. extractionThe mixture is extracted with methylene chloride
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue is dissolved in 0.54 l of ether
  4. customcrystallized at about -20°

Sources & evidence

ORD record
ord-a8f95aeb9d8c4ca687238f9da1bca3e0
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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