Hydrochloric Acid → 5-[(3-fluorobenzyl)sulfanyl]-3-hydroxypyridin-2(1H)-one

HRID 709088Notes

Reaction equation

HRID 709088 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][S:6][C:7]1[CH:8]=[C:9]([O:17]COC)[C:10]([O:13]COC)=[N:11][CH:12]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][S:6][C:7]1[CH:8]=[C:9]([OH:17])[C:10](=[O:13])[NH:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867315445-[(3-Fluorobenzyl)sulfanyl]-2,3-bis(methoxymethoxy)pyridine2×

Product 1

HCID 711871545-[(3-fluorobenzyl)sulfanyl]-3-hydroxypyridin-2(1H)-oneYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 5-[(3-fluorobenzyl)sulfanyl]-2,3-bis(methoxymethoxy)pyridine (Intermediate 43; 690 mg, 2.03 mmol) in dioxane (4 ml) was added a solution of hydrogen chloride in dioxane (4.0 M; 2.54 ml, 10.17 mmol) and the reaction stirred for 16 hours before being concentrated in vacuo. The crude product was recrystallised from ethanol and water to yield 5-[(3-fluorobenzyl)sulfanyl]-3-hydroxypyridin-2(1H)-one as a pale grey solid (309 mg, 61%).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe crude product was recrystallised from ethanol and water

Sources & evidence

ORD record
ord-d412914bf4434859bc801b1fce579c4e
Source dataset
uspto-grants-2015_11
Patent number
US09180122B2

Reaction notes

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