Sodium Carbonate → 4-Chloro-3-(3-fluoropyridin-4-yl)benzenamine

HRID 30800Notes

Reaction equation

HRID 30800 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[F:17].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[F:17]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 690048774-(2-Chloro-5-nitrophenyl)-3-fluoropyridine

Product 1

HCID 690046574-Chloro-3-(3-fluoropyridin-4-yl)benzenamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

4-(2-chloro-5-nitrophenyl)-3-fluoropyridine (1 eq) was stirred with Iron (0), (3 eq), in acetic acid for 10 hours at room temperature. Reaction neutralized with sodium carbonate and filtered to remove iron. Reaction partitioned between ethyl acetate and water. Organic layer separated and washed with brine, dried over sodium sulfate and concentrated to give 4-chloro-3-(3-fluoropyridin-4-yl)benzenamine. HPLC=1.72 min; MS: MH+=223.

Workup

  1. customReaction
  2. filtrationfiltered
  3. customto remove iron
  4. customReaction
  5. custompartitioned between ethyl acetate and water
  6. customOrganic layer separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ffdfce5132e246cd8bd1d434fc023b11
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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