Acetic Acid → HCID 13813702, compound

HRID 652590Notes

Reaction equation

HRID 652590 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[C:5]=1[C:6]#[N:7])([O-])=O.C(O)(=O)C.C>[Fe].CC(O)C>[NH2:1][C:4]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[C:5]=1[C:6]#[N:7]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 297MethaneHCID 12028174Benzonitrile, 2,3-dimethoxy-6-nitro-

Product 1

HCID 13813702HCID 13813702, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Procedure

Iron powder (8.70 g, 156 mmol) was added to a suspension of (9.30 g, 44.5 mmol) of 2-nitro-5,6-dimethoxybenzonitrile in an acetic acid (30 ml) and 2-propanol (30 ml) mixture. The mildly exothermic reaction which resulted was allowed to reach 100° and a gentle reflux was maintained for 1 hour with application of heat. Charcoal (10 g) was added, the reaction mixture filtered, and the solid residue obtained was washed with hot 2-propanol (100 ml). The combined filtrates were evaporated to an oily residue which was redissolved in CHCl3 and washed with 5% aqueous NaHCO3 and saturated aqueous NaCl solution. The CHCl3 phase was dried with Na2SO4 and evaporated in vacuo to yield 7.0 g (88.4%) of the target compound as an oil.

Workup

  1. customThe mildly exothermic reaction which
  2. customresulted
  3. customto reach 100°
  4. temperaturea gentle reflux
  5. temperaturewas maintained for 1 hour with application
  6. temperatureof heat
  7. filtrationthe reaction mixture filtered
  8. customthe solid residue obtained
  9. washwas washed with hot 2-propanol (100 ml)
  10. customThe combined filtrates were evaporated to an oily residue which
  11. dissolutionwas redissolved in CHCl3
  12. washwashed with 5% aqueous NaHCO3 and saturated aqueous NaCl solution
  13. dry with materialThe CHCl3 phase was dried with Na2SO4
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-23b6725b49cb4a0f97e93e69ee856e39
Source dataset
uspto-grants-1987_06
Patent number
US04672116

Reaction notes

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