HCID 66650497, compound → HCID 66650419, compound

HRID 1293589Notes

Reaction equation

HRID 1293589 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) was added in small portions over 5 min to a stirred suspension of finely grinded 5-ethoxy-2-nitro-4-trifluoromethyl-benzonitrile from step 3 (42.79 g, 164.5 mmol) in MeOH (85 mL) and conc. HCl (102 mL) with water bath cooling keeping the internal temperature at 40–50° C. The resulting mixture was stirred for further 1 h at ca. 50° C. and then poured into ice cold H2O (700 mL). The precipitate was filtered, washed with water, dried, and dissolved in boiling EtOH (800 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 yellow solid (31.81 g, 84%), which was used without further purification. MS (EI) 230.1 [M].

Workup

  1. temperaturecooling
  2. customat 40–50° 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-e89d4339a15a437ab35f2acfd380d813
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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