Methanol → 3-(3-FLUORO-BENZYLOXY)-PHENYLAMINE

HRID 607284Notes

Reaction equation

HRID 607284 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1.[Cl-].[NH4+].CO.O1CCCC1>[Fe].O>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 52891771HCID 52891771, compound

Product 1

HCID 64860233-(3-FLUORO-BENZYLOXY)-PHENYLAMINEYield 93.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a solution of the product from Example 199A (0.494 g, 2.0 mmol), iron powder (0.56 g, 10.0 mmol) and ammonium chloride (0.54 g, 10.0 mmol) in a methanol (20 mL), tetrahydrofuran (20 mL), and water (10 mL) solution was heated to reflux for 2 hours. The resultant mixture was filtered through a pad of celite, and the filtrate was concentrated. Then ethyl acetate was added, stirred for 30 minutes, filtered and concentrated under vacuum to provide the title compound (0.405 g, 93%).

Workup

  1. temperatureto reflux for 2 hours
  2. filtrationThe resultant mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated
  4. additionThen ethyl acetate was added
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4f7554e8e7fb4c15b50ea1adde401b13
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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