Acetic Acid → 3-Hydroxy-2-phenyl-6-azabenzo[b]thiophene

HRID 35539Notes

Reaction equation

HRID 35539 reaction equation
[C:1]1([CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[C:14](OC)=[S:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C(O)(=[O:22])C>O1CCCC1.CN(C)C=O>[OH:22][C:8]1[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:14]=2[S:15][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 86742398Methyl 3-phenylmethylthiopyridine-4-carboxylate

Product 1

HCID 146738203-Hydroxy-2-phenyl-6-azabenzo[b]thiopheneYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4.8 g (19 mmol) of methyl 3-phenylmethylthiopyridine-4-carboxylate in 10 mL of tetrahydrofuran was added to a slurry of 2.40 g (60 mmol) of 60% sodium hydride in 10 mL of N,N-dimethylformamide and the resulting mixture was stirred at 60° C. for 3 hours. The solution was poured onto ice water and acidified with glacial acetic acid. The filtrate was collected to afford 1.6 g (38%) of white solid.

Workup

  1. additionThe solution was poured onto ice water
  2. customThe filtrate was collected

Sources & evidence

ORD record
ord-5c9fce38eb274a838188106b5d0e387b
Source dataset
uspto-grants-1988_08
Patent number
US04767766

Reaction notes

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