Sodium Hydroxide → 3,5-Diaminobenzonitrile

HRID 1190897Notes

Reaction equation

HRID 1190897 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[C:7]#[N:8])([O-])=O.Cl[Sn]Cl.[OH-].[Na+]>Cl>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([NH2:12])[CH:11]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 20062Benzonitrile, 3,5-dinitro-HCID 24479Stannous Chloride

Product 1

HCID 128973293,5-DiaminobenzonitrileYield 57%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 3,5-dinitrobenzonitrile (5.0 g, 25.89 mmol) in 20 mL of HCl 1M, was added SnCl2 (34.4 g, 7 eq). The reaction mixture was stirred at room temperature for 2 h and then cooled to 0° C. The mixture was made alkaline with a 50% aqueous solution of NaOH and the precipitate was removed by filtration. The filtrate was extracted with ethyl acetate and the combined organic layers were evaporated. The residue and the precipitate were purified by flash chromatography on silica gel (DCM/MeOH//95/5) to yield expected compound as an orange solid (1.95 g, 57% yield). m/z (ESI) 134.0 [M+H]+.

Workup

  1. temperaturecooled to 0° C
  2. customthe precipitate was removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate
  4. customthe combined organic layers were evaporated
  5. customThe residue and the precipitate were purified by flash chromatography on silica gel (DCM/MeOH//95/5)

Sources & evidence

ORD record
ord-c9d06e2ce5ab4de282e6822838a95cc4
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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