Hydrochloric Acid → HCID 21790893, compound

HRID 2398985Notes

Reaction equation

HRID 2398985 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:12][CH2:11][CH2:10][C:9](=[N:13]O)[CH:8]=2)[CH:2]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].Cl>C(O)(=O)C>[C:15]([NH:13][C:9]1[CH:8]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:12]=[CH:11][CH:10]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 7918Acetic AnhydrideHCID 73181968HCID 73181968, compound

Product 1

HCID 21790893HCID 21790893, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture containing 28.9 g. of 3-(3-pyridinyl)-2-cyclohexen-1-one oxime, 42 ml. of acetic acid and 42 ml. of acetic anhydride was passed gaseous hydrogen chloride whereupon the temperature rose to about 120° C. The hydrogen chloride was passed continuously into the reaction mixture until the temperature fell to about 50° C. The reaction mixture was allowed to stand for three hours and then concentrated in vacuo to yield, as a glassy material, 3-(3-acetamidophenyl)pyridine. To this material was added 100 ml. of water and 25 ml. of concentrated hydrochloric acid and the resulting mixture was refluxed for sixteen hours and concentrated in vacuo to yield a yellow solid. The solid was taken up in water and the solution was made alkaline with 35% aqueous sodium hydroxide solution. The alkaline solution was extracted three times with ethylene dichloride. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield an oil. The oil was distilled under reduced pressure, collecting the fraction boiling at 141°-145° C. at 0.15 mm. to yield, first as a yellow oil which crystallized on cooling, 17.7 g. of 3-(3-aminophenyl)pyridine, m.p. 72°- 74° C.

Workup

  1. additionTo a mixture containing 28.9 g
  2. customrose to about 120° C
  3. customfell to about 50° C
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-704e0fcb5a5a4f4e96064980d8c9d680
Source dataset
uspto-grants-1977_05
Patent number
US04026900

Reaction notes

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