Hydrochloric Acid → 3-amino-2-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]pyridine

HRID 2086793Notes

Reaction equation

HRID 2086793 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C(=O)(O)[O-].[Na+]>CO.[Fe]>[NH2:1][C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 227244742-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]-3-nitropyridine

Product 1

HCID 227243163-amino-2-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]pyridineYield 65.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-nitro-2-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]pyridine (493 mg), iron powder (0.35 g) and hydrochloric acid (35%, 1 ml) in methanol (5 ml) was stirred under reflux for 4 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 3-amino-2-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]pyridine (291 mg).

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic phase was washed with aqueous sodium bicarbonate 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-fdf7f43add2943e39b9cf76d4f8c6827
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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