2-Bromopropane → HCID 22145815, compound

HRID 1994344Notes

Reaction equation

HRID 1994344 reaction equation
[OH:1][C:2]1[C:3]([CH3:12])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[S:8].[CH:13](Br)([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:13]([O:1][C:2]1[C:3]([CH3:12])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[S:8])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 22145740HCID 22145740, compound

Product 1

HCID 22145815HCID 22145815, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 5-hydroxy-6-methylthionicotinoate (3 g), isopropyl bromide (2.1 mL) and anhydrous potassium carbonate (3 g) in dry dimethylformamide (35 mL) is stirred and heated at 60±5° C. for 18 hours. After cooling the solvent is removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase is washed with brine and dried (MgSO4). Evaporation gives a brown oil which is purified by flash chromatography (pentane/ethyl acetate 4:1 v/v as eluent on silica) to give methyl 5-isopropyloxy-6-methylthionicotinoate (2.36 g) as a pale yellow oil. [Elemental analysis: —C, 54.40; H, 6.24; N, 5.88%. calculated: —C, 54.75; H, 6.27; N, 5.81%.].

Workup

  1. temperatureAfter cooling the solvent
  2. customis removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic phase is washed with brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation
  7. customgives a brown oil which
  8. customis purified by flash chromatography (pentane/ethyl acetate 4:1 v/v as eluent on silica)

Sources & evidence

ORD record
ord-ab24eb68c9f847b4aad51ea251319fc0
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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