Hydrochloric Acid → 3,3'-Diaminobenzidine

HRID 1673070Notes

Reaction equation

HRID 1673070 reaction equation
O.O.Cl[Sn]Cl.Cl.[N+:7]([C:10]1[CH:11]=[C:12]([C:17]2[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([N+:24]([O-])=O)[CH:18]=2)[CH:13]=[CH:14][C:15]=1[NH2:16])([O-])=O>>[NH2:7][C:10]1[CH:11]=[C:12]([C:17]2[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([NH2:24])[CH:18]=2)[CH:13]=[CH:14][C:15]=1[NH2:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 31067203,3'-Dinitrobenzidine

Product 1

HCID 70713,3'-DiaminobenzidineYield 74%

Procedure

A 50 ml single neck round bottomed flask equipped with condenser, and stirring magnetic bar were placed SnCl2.2H2O (12 g, 53 mmol) and 25 ml concentrated hydrochloric acid and reaction mixture was stirred and than 3,3′-dinitrobenzidine (DNB) of formula 2 where in R═H (2.16 g, 7.9 mmol) was added in small portions over 15 minute to maintain the reaction temperature less than 60° C. The thick slurry was then stirred for additional 2 hours at 40° C. to complete the reduction. The salt of the tetramine was precipitated out, which was neutralized with cold 10% NaOH solution and the solid filtered out, washed with water dried under vacuum to give 3,3′-diaminobenzidine (DAB) in 74% yield (1.26 g).

Workup

  1. customA 50 ml single neck round bottomed flask equipped with condenser
  2. additionwas added in small portions over 15 minute
  3. temperatureto maintain the reaction temperature less than 60° C
  4. stirringThe thick slurry was then stirred for additional 2 hours at 40° C.
  5. customThe salt of the tetramine was precipitated out
  6. filtrationthe solid filtered out
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-e26bdacde6364c4d8ee4788fdfaeda02
Source dataset
uspto-grants-2011_08
Patent number
US07999112B2

Reaction notes

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