Hydrochloric Acid → HCID 22724193, compound

HRID 2086794Notes

Reaction equation

HRID 2086794 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:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C(=O)(O)[O-].[Na+]>C(O)C.[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]=[CH:21][N: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 227240493-nitro-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridine

Product 1

HCID 22724193HCID 22724193, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-nitro-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridine (1.38 g), iron powder (1.0 g) and hydrochloric acid (35D, 3.0 ml) in ethanol (10 ml) was stirred at 80° C. for 2 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 residue was chromatographed on silica gel column (8% methanol in chloroform) to give 3-amino-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridine (1.14 g) as powder.

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel column (8% methanol in chloroform)

Sources & evidence

ORD record
ord-4ffb8a049c8c4636b19a8a4dea0720b4
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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