Tetrahydrofuran → HCID 178479388, compound

HRID 412700Notes

Reaction equation

HRID 412700 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:12])=[NH:11])=[CH:5][C:4]=1[N+:13]([O-])=O.O1CCCC1>[Pd].CO>[ClH:1].[NH2:13][C:4]1[CH:5]=[C:6]([NH:9][C:10]([NH2:12])=[NH:11])[CH:7]=[CH:8][C:3]=1[NH2:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 178479389HCID 178479389, compound

Product 1

HCID 178479388HCID 178479388, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture comprising N-(4-amino-3-nitrophenyl)guanidine hydrochloride (12.0 g, 51.8 mmol), 10% palladium on carbon (1.0 g), tetrahydrofuran (100 mL) and methanol (100 mL) was hydrogenated at one atmosphere, filtered and concentration in vacuo to provide N-(3,4-diaminophenyl)guanidine hydrochloride (10.3 g, 98% yield) as a dark solid; 1H-NMR (300 MHz, DMSO-d6): 9.4 (s), 7.2 (s), 6.5 (d), 6.3 (s), 6.2 (d), 4.7 (s).

Workup

  1. filtrationfiltered
  2. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-17443b44ebe14857bfd6249e5af281bc
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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