Dimethyl Sulfate → HCID 68765199, compound

HRID 2362829Notes

Reaction equation

HRID 2362829 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[N:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].[C:25]([O-])(O)=O.[Na+].S(OC)(OC)(=O)=O>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[N:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([O:13][CH3:25])=[O:12]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 687626192-(3-Fluoro-3'-hydroxybiphenyl-4-ylamino)nicotinic acid

Product 1

HCID 68765199HCID 68765199, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-(3-fluoro-3′-hydroxybiphenyl-4-ylamino)nicotinic acid (1 g, 3.08 mmol) and NaHCO3 (0.5 g, 6.17 mmol) in acetone (20 ml) was added dropwise dimethyl sulphate (0.47 g, 3.70 mmol). The mixture was heated to reflux overnight and then concentrated. Ethyl acetate was added to the crude and washed twice with 4% solution of NaHCO3 and brine. The organic phase was then dried over MgSO4 and concentrated in vacuo to afford 0.4 g of solid beige pure enough for the next synthetic step. Yield=36%

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. additionEthyl acetate was added to the crude
  5. washwashed twice with 4% solution of NaHCO3 and brine
  6. dry with materialThe organic phase was then dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e4a390b08ae4f74bb33d8b6a5dfe50a
Source dataset
uspto-grants-2014_04
Patent number
US08691852B2

Reaction notes

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