Hydrochloric Acid → 6.7-dihydrothieno[3.2.c]pyridin-4(5H)-one

HRID 1701510Notes

Reaction equation

HRID 1701510 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH2:5][CH2:4][N:3]1C(=O)C.Cl>C(O)C>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH2:5][CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20346849HCID 20346849, compound

Product 1

HCID 203468586.7-dihydrothieno[3.2.c]pyridin-4(5H)-oneYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An initially heterogeneous mixture of 4-oxo-5-acetyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (13.6 g; 0.069 mole) from Example 5, ethanol (50 ml) and 6 N hydrochloric acid (50 ml) is stirred for 4 hours at room temperature. The reaction mixture is concentrated in vacuo, the residue is made slightly basic by addition of sodium hydroxide and is then extracted with methylene chloride. The organic extracts are washed with water, dried over sodium sulfate and evaporated to dryness. The resulting residue is recrystallized from isopropanol-diisopropyl ether, to give white crystals, M.p.=94° C. Yield: 70%.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionthe residue is made slightly basic by addition of sodium hydroxide
  3. extractionis then extracted with methylene chloride
  4. washThe organic extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe resulting residue is recrystallized from isopropanol-diisopropyl ether
  8. customto give white crystals, M.p.=94° C

Sources & evidence

ORD record
ord-aad55a20070d4e9fb55e43116e1f0c9c
Source dataset
uspto-grants-1980_03
Patent number
US04193997

Reaction notes

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