Hydrochloric Acid → N2-(3-Chlorophenyl)-2,3-pyridinediamine

HRID 2086780Notes

Reaction equation

HRID 2086780 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl.C(=O)(O)[O-].[Na+]>C(O)C.[Fe]>[NH2:15][C:14]1[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 12588336HCID 12588336, compound

Product 1

HCID 12588337N2-(3-Chlorophenyl)-2,3-pyridinediamineYield 81.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(3-chlorophenylamino)-3-nitropyridine (394 mg), hydrochloric acid (35% 1.3 ml) and iron powder (0.44 g) in ethanol (5 ml) was refluxed for 15 minutes. The mixture was poured into aqueous sodium bicarbonate solution and extracted with ethyl acetate twice. The combined organic solution was washed with aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 3-amino-2-(3-chlorophenylamino)pyridine (281 mg).

Workup

  1. temperaturewas refluxed for 15 minutes
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic solution was washed with aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-62545148ded04e09845814c12e7889e2
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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