4-Amino-3-nitrobenzimidamide hydrochloride → 3,4-Diaminobenzimidamide hydrochloride

HRID 1961494Notes

Reaction equation

HRID 1961494 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][C:4]=1[N+:12]([O-])=O>[OH-].[OH-].[Pd+2].CO>[ClH:1].[NH2:12][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[NH2:2])[C:7]([NH2:9])=[NH:8]

Participants

4

Reactant 1

HCID 673560924-Amino-3-nitrobenzimidamide hydrochloride

Product 1

HCID 221255323,4-Diaminobenzimidamide hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

A suspension of 4-amino-3-nitrobenzamidine monohydrochloride (15 g, 69 mmol) and Pearlman's catalyst [Pd(OH)2, 1.0 g, 7.12 mmol) in methanol (200 mL) was shaken under hydrogen atmosphere 50 psi for 1.5 h. The suspension was filtered through Celite and the filtrate was added dropwise to anhydrous diethyl ether (400 mL) to precipitate 3,4-diaminobenzamidine monohydrochloride as a tan solid.

Workup

  1. filtrationThe suspension was filtered through Celite
  2. additionthe filtrate was added dropwise to anhydrous diethyl ether (400 mL)
  3. customto precipitate 3,4-diaminobenzamidine monohydrochloride as a tan solid

Sources & evidence

ORD record
ord-e37fba752b494bc783dbf84895e147d0
Source dataset
uspto-grants-2013_04
Patent number
US08415328B2

Reaction notes

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