Hydrochloric Acid → Picolinic acid, 5-(3-chloropropoxy)-

HRID 443436Notes

Reaction equation

HRID 443436 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][Cl:15])=[CH:7][N:6]=1)=[O:4].Cl>>[Cl:15][CH2:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 537524315-(3-Chloropropoxy)-2-pyridine-carboxylic acid methyl ester

Product 1

HCID 3055221Picolinic acid, 5-(3-chloropropoxy)-

Procedure

A mixture of 9.0 g of 5-(3-chloropropoxy)-2-pyridinecarboxylic acid methyl ester and 100 ml of 6N-hydrochloric acid is heated on a steam bath for 30 minutes. After that, the solution is cooled and evaporated to a residue. To the residue is added water and the resulting suspension is adjusted to pH 5 with saturated aqueous solution of sodium bicarbonate. The precipitated product is collected, dissolved in ethyl acetate and filtered. The filtrate is evaporated to a small volume. To the concentrate is added hexane to yield 5-(3-chloropropoxy)-2-pyridinecarboxylic acid melting at 120°-121°.

Workup

  1. temperatureis heated on a steam bath for 30 minutes
  2. temperatureAfter that, the solution is cooled
  3. customevaporated to a residue
  4. additionTo the residue is added water
  5. customThe precipitated product is collected
  6. dissolutiondissolved in ethyl acetate
  7. filtrationfiltered
  8. customThe filtrate is evaporated to a small volume
  9. additionTo the concentrate is added hexane

Sources & evidence

ORD record
ord-e619028b1d1d41e3a2de6259e9cc5c4a
Source dataset
uspto-grants-1981_04
Patent number
US04260620

Reaction notes

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