HCID 86086323, compound → HCID 86086326, compound

HRID 1784539Notes

Reaction equation

HRID 1784539 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O>CO.Cl.[Fe]>[NH2:1][C:4]1[CH:11]=[C:10]([C:12]([F:14])([F:15])[F:13])[C:9]([O:16][CH2:17][C:18]([F:19])([F:20])[F:21])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 1

HCID 86086323HCID 86086323, compound

Product 1

HCID 86086326HCID 86086326, compoundYield 88.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

Iron powder (15.80 g, 283.0 mmol) was added in small portions over 5 min to a stirred suspension of finely grinded 2-nitro-5-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzonitrile from step 3 (19.93 g, 63.4 mmol) in MeOH (32 mL) and conc. HCl (40 mL) with water bath cooling keeping the internal temperature at 25-35° C. The resulting mixture was stirred for further 1 h at ca. 30° C. and then poured into ice cold H2O (400 mL). The precipitate was filtered, washed with water, dried, and dissolved in boiling EtOH (400 mL), activated carbon (ca. 10 g) was added, the mixture was refluxed for 45 min, the hot solution was filtered and evaporated to dryness to leave a dark green solid (15.96 g, 84%), which was further purified by silica gel column chromatography with heptane/EtOAc 4:1 to give the title compound as a yellow solid (14.56 g, 81%). MS (ISN) 283 [M−H].

Workup

  1. temperaturecooling
  2. customat 25-35° C
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried
  6. dissolutiondissolved
  7. additionwas added
  8. temperaturethe mixture was refluxed for 45 min
  9. filtrationthe hot solution was filtered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-6123c6982ce24b7ea88eee8dc137d7fe
Source dataset
uspto-grants-2009_03
Patent number
US07504404B2

Reaction notes

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