Sodium Carbonate → 3-(3-Chloro(4-pyridyl))-4-methylphenylamine

HRID 1915675Notes

Reaction equation

HRID 1915675 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=1[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:9]=1[CH3:17]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 220408203-Chloro-4-(2-methyl-5-nitrophenyl)pyridine

Product 1

HCID 220404863-(3-Chloro(4-pyridyl))-4-methylphenylamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To the mixture containing 3-chloro-4-(2-methyl-5-nitrophenyl)pyridine in acetic acid was added Fe dust (5 eq) and the resulting mixture was stirred at ambient temperature for 6 h. To it was then added saturated sodium carbonate to bring it to neutral pH and extracted with ethyl acetate. The organic layer was washed with brine and dried with sodium sulfate and concentrated and passed through a plug of silica to yield 3-(3-chloro(4-pyridyl))-4-methylphenylamine. MS: MH+=218.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-19777878cd084f2d867e7d3f7e4b7ffe
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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