Formic Acid → HCID 178509527, compound

HRID 219574Notes

Reaction equation

HRID 219574 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[OH-].[Na+].[CH:13](O)=O>>[NH:10]1[C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[N:1]=[CH:13]1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 178509527HCID 178509527, compoundYield 82%

Conditions

Temperature
100 °C

Procedure

3,4-Diaminobenzonitrile (1.0 g; 7.5 mmol) was dissolved in formic acid (3 mL) and heated at 100° C. for 1.5 hours. The mixture was cooled, neutralised with 10% sodium hydroxide and the resulting precipitate isolated by filtration and dried in vacuo to yield the title compound as a brown solid (890 mg; 82%). 1H NMR (DMSO-d6) δ 8.50 (1H, s), 8.19 (1H, s), 7.79 (1H, d, J=8.3 Hz), 7.62 (1H, dd, J=8.3, 1.54 Hz). LC/MS (Method C): 144 (M+H)'. HPLC (Method F) Rt=2.14 min (Purity: 99.4%).

Workup

  1. temperatureThe mixture was cooled
  2. customthe resulting precipitate isolated by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-64e598bebb6445a9a1aa5a8ba2908631
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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