Sodium Hydroxide → 6-Butyryl-7-chloro-3-methoxythieno[3,2-b]pyridine

HRID 2107628Notes

Reaction equation

HRID 2107628 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[NH:8][CH:9]=[C:10]([C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[C:11](=O)[C:6]=2[S:5][CH:4]=1.[OH-].[Na+].P(Cl)(Cl)([Cl:22])=O>>[C:13]([C:10]1[C:11]([Cl:22])=[C:6]2[S:5][CH:4]=[C:3]([O:2][CH3:1])[C:7]2=[N:8][CH:9]=1)(=[O:17])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 230461623-Methoxy-6-butyrylthieno[3,2-b]pyridin-7(4H)-one

Product 1

HCID 230461496-Butyryl-7-chloro-3-methoxythieno[3,2-b]pyridine

Procedure

3-Methoxy-6-butyrylthieno[3,2-b]pyridin-7(4H)-one (3 g) and phosphorus oxychloride (10 ml) were heated under reflux for one hour. The reaction mixture was poured onto ice water (100 g) stirred for 30 minutes and then basified with 40% sodium hydroxide solution cooling with ice, then extracted with chloroform (3×100 ml). The chloroform extracts were combined dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a brown solid, 3.1 g, m.p. 76°-78°.

Workup

  1. temperatureunder reflux for one hour
  2. additionThe reaction mixture was poured onto ice water (100 g)
  3. temperaturecooling with ice
  4. extractionextracted with chloroform (3×100 ml)
  5. dry with materialThe chloroform extracts were combined dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give a brown solid, 3.1 g, m.p. 76°-78°

Sources & evidence

ORD record
ord-15da17b956644bc9abb72f70f4cce27c
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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