Formic Acid → HCID 178509527, compound

HRID 400715Notes

Reaction equation

HRID 400715 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[CH:11](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:11]1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 178509527HCID 178509527, compoundYield 98%

Procedure

A solution of 3,4-diaminobenzonitrile (1 g; 7.51 mmol) in formic acid (40 mL) was heated at reflux for 3 hours then concentrated in vacuo to give a brown oily residue. It was extracted with EtOAc from a saturated aqueous solution of NaHCO3, dried over MgSO4 and evaporated under vacuum to give the title compound as a light pink solid (1.05 g, 98%). 1H NMR (DMSO-d6): δ 12.97 (br s, 1H), 8.48 (s, 1H), 8.16 (d, J=0.8 Hz, 1H), 7.76 (d, J=8.3 Hz, 1H), 7.59 (dd, J=8.3, 1.5 Hz, 1H). LC/MS (Method B): 144.1 (M+H)+.

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationthen concentrated in vacuo
  3. customto give a brown oily residue
  4. extractionIt was extracted with EtOAc from a saturated aqueous solution of NaHCO3
  5. dry with materialdried over MgSO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-cd33457d41ef465e90c05beda3037680
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

Loading…