Hydrochloric Acid → HCID 22724080, compound

HRID 2231006Notes

Reaction equation

HRID 2231006 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)[CH:7]=1.Cl.C(=O)(O)[O-].[Na+]>CO.[Fe]>[NH2:16][C:12]1[CH:11]=[C:10](/[CH:9]=[CH:8]/[C:6]2[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[CH:7]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22724426HCID 22724426, compound

Product 1

HCID 22724080HCID 22724080, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-chloro-5-[(E)-2-(3-nitrophenyl)vinyl]pyridine (2.99 g), iron powder (2.6 g) and hydrochloric acid (35%, 8 ml) in methanol (50 ml) was stirred at 60° C. for 3 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-[(E)-2-(3-aminophenyl)vinyl]-5-chloropyridine (1.33 g).

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 resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-d9324e6064bd4914980a9a20eb9ef371
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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