Ethanol → HCID 59280088, compound

HRID 1518133Notes

Reaction equation

HRID 1518133 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([N+:19]([O-])=O)[CH:13]=1.CCO.[Cl-].[NH4+]>[Fe].O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH2:19])[CH:13]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 50994194HCID 50994194, compound

Product 1

HCID 59280088HCID 59280088, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

2′-Fluoro-3-nitro-6′-trifluoromethyl-biphenyl-4-ylamine (754 mg, 2.51 mmol, as prepared in the previous step) was placed in a 40 mL vial equipped with a magnetic stir bar, then EtOH (20 mL) and water (5 mL) were added. Ammonium chloride (10 eq., 1.34 g, 25.1 mmol) was added as a solid, and then iron powder (5 eq., 701 mg, 12.6 mmol) was added. The vial was tightly capped and placed in a heating block where the reaction was stirred at 80° C. for 14 h. The reaction was cooled to rt, poured into water, and extracted three times with EtOAc (40 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give 662 mg (98%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 7.52 (d, J=7.8 Hz, 1H), 7.39 (td, J=7.9, 5.7 Hz, 1H), 7.25-7.32 (m, 1H), 6.71-6.77 (m, 1H), 6.60-6.67 (m, 2H), 3.45 (br. s., 4H).

Workup

  1. customvial equipped with a magnetic stir bar
  2. customThe vial was tightly capped
  3. temperatureThe reaction was cooled to rt
  4. extractionextracted three times with EtOAc (40 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-04e971d8f7f94d08be8060dce270353d
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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