Water → HCID 20483868, compound

HRID 648009Notes

Reaction equation

HRID 648009 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH2:15][CH:16]([C:17]#N)[C:11]3=[CH:10][CH:9]=2)=[S:7])=[CH:4][CH:3]=1.[OH2:21].[OH-:22].[K+]>C(O)CO>[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH2:15][CH:16]([C:17]([OH:22])=[O:21])[C:11]3=[CH:10][CH:9]=2)=[S:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 20484250HCID 20484250, compound

Product 1

HCID 20483868HCID 20483868, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of the resulting nitrile (1.5 g., 0.005 moles) in ethylene glycol (20 ml.) containing water (1.6 ml.) and potassium hydroxide (1.65 g.) is heated in an oil bath at 110°-120°, in a nitrogen atmosphere, for 2.5 hours. The solution is cooled to room temperature, it is poured into water (60 ml.) and extracted with ether (2×30 ml.). The aqueous alkaline phase is cooled to 5° C. and made acidic to pH-4. The product is extracted into ethyl acetate (3×100 ml.), the extract is washed with water, dried, and evaporated in vacuo. The residue is crystallized from dichloromethane-methanol to give 3-p-methylthiobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid, m.p. 174°-175°.

Workup

  1. temperatureis heated in an oil bath at 110°-120°, in a nitrogen atmosphere, for 2.5 hours
  2. extractionextracted with ether (2×30 ml.)
  3. temperatureThe aqueous alkaline phase is cooled to 5° C.
  4. extractionThe product is extracted into ethyl acetate (3×100 ml.)
  5. washthe extract is washed with water
  6. customdried
  7. customevaporated in vacuo
  8. customThe residue is crystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-260ff91e4fa047ffbe795266966b8717
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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