HCID 66650497, compound → HCID 66650419, compound

HRID 1990810Notes

Reaction equation

HRID 1990810 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([N+:12]([O-])=O)=[C:8]([CH:11]=1)[C:9]#[N:10])[CH3:2]>CO.Cl.[Fe]>[NH2:12][C:7]1[CH:6]=[C:5]([C:15]([F:17])([F:18])[F:16])[C:4]([O:3][CH2:1][CH3:2])=[CH:11][C:8]=1[C:9]#[N:10]

Participants

5

Reactant 1

HCID 66650497HCID 66650497, compound

Product 1

HCID 66650419HCID 66650419, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Iron powder (40.96 g, 733 mmol, 1.0 equiv) was added in small portions over 5 min to a stirred suspension of finely grinded 5-ethoxy-2-nitro-4-trifluoromethyl-benzonitrile (42.79 g, 164.5 mmol, 4.5 equiv) in methanol (85 mL) and conc. HCl (102 mL) which was cooled with a water bath to keep the internal temperature at 40-50° C. The resulting mixture was stirred for an additional hour at ca. 50° C. and then poured into ice cold water (700 mL). The precipitate was filtered, washed with water, dried, and dissolved in boiling ethanol (800 mL). Activated carbon (ca. 10 g) was added, the mixture refluxed for 45 min, the hot solution filtered and the organic phase evaporated under reduced pressure to dryness to leave 31.8 g (84%) of the title compound as a yellow solid which was used without further purification. MS (EI): 230.1 [M]+.

Workup

  1. temperaturewas cooled with a water bath
  2. customat 40-50° C
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried
  6. dissolutiondissolved
  7. additionActivated carbon (ca. 10 g) was added
  8. temperaturethe mixture refluxed for 45 min
  9. filtrationthe hot solution filtered
  10. customthe organic phase evaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-6bad69af9d8941e7bd63578d27a1201f
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

Loading…