Sodium Hydroxide → 5-Iodo-6-isopropoxynicotinic acid

HRID 1820982Notes

Reaction equation

HRID 1820982 reaction equation
[I:1][C:2]1[C:3]([O:13][CH:14]([CH3:16])[CH3:15])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C(O)(C)C>[I:1][C:2]1[C:3]([O:13][CH:14]([CH3:16])[CH3:15])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68851282Ethyl 5-iodo-6-isopropoxynicotinate

Product 1

HCID 688516415-Iodo-6-isopropoxynicotinic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 210 mg (0.63 mmol) of ethyl 5-iodo-6-isopropoxynicotinate (from Step B) in 2.5 mL isopropanol was added 250 μL of 5.0 N NaOH. After stirring at rt for S h, the reaction mixture was partitioned between EtOAc (10 mL) and 1.0 N HCl (10 mL). The organic layer was separated, washed with brine (3×5 mL), dried over MgSO4, and concentrated to give 190 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.44 (d, J=6.4, 6H), 5.44 (m, 1H), 8.66 (d, J=2.1, 1H), 8.83 (d, J=2.1, 1H).

Workup

  1. customthe reaction mixture was partitioned between EtOAc (10 mL) and 1.0 N HCl (10 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (3×5 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-650065766f3f4577838d75b71f8c19c5
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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