5-Chloro-2-nitro-N,N'-dipropylbenzamidine → 2-Amino-5-chloro-N,N'-dipropylbenzamidine

HRID 1167135Notes

Reaction equation

HRID 1167135 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([CH:16]=1)[C:7]([NH:12][CH2:13][CH2:14][CH3:15])=[N:8][CH2:9][CH2:10][CH3:11].[H][H]>C1COCC1.[Ni].CCO>[NH2:17][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][C:6]=1[C:7]([NH:12][CH2:13][CH2:14][CH3:15])=[N:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 229958345-Chloro-2-nitro-N,N'-dipropylbenzamidineHCID 178418361HCID 178418361, compound

Product 1

HCID 112305382-Amino-5-chloro-N,N'-dipropylbenzamidine

Reagents, catalysts & solvents 2

HCID 86745698ethanol Raney-nickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

27.4 g (0.097 mol) of 5-chloro-2-nitro-N,N′-dipropylbenzamidine are dissolved in 200 ml of THF and are hydrogenated in the presence of 15 g Ra—Ni/EtOH at room temperature for 5 hours (take up of hydrogen: 94%). Then the catalyst is filtered off and the solvent removed in a water jet vacuum. The residue is purified by column chromatography on silica gel (eluant: hexane/THF 1:1, then THF). Yield: 11.9 g of 2-amino-5-chloro-N,N′-dipropylbenzamidine in the form of a brown oil (1H-NMR (CDCl3);.ppm/multiplicity/number of H's): 0.91/m/6H; 1.56/m/4H; 3.10/m (broad)/4H, 3.75/s(broad)/2H; 6.63/d/1H; 7.02/d/1H; 7.10/dd/1H.

Workup

  1. filtrationThen the catalyst is filtered off
  2. customthe solvent removed in a water jet vacuum
  3. customThe residue is purified by column chromatography on silica gel (eluant

Sources & evidence

ORD record
ord-fac5a46d05974ae085bc9b3d37158014
Source dataset
uspto-grants-2003_09
Patent number
US06617330B2

Reaction notes

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