Water → HCID 59799624, compound

HRID 2368384Notes

Reaction equation

HRID 2368384 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].I[CH2:16][C:17]([NH2:19])=[O:18].O>CN(C=O)C>[NH2:3][C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:16][C:17]([NH2:19])=[O:18])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 3727IodoacetamideHCID 24758Sodium hydrideHCID 819940methyl 2-amino-5-hydroxybenzoate

Product 1

HCID 59799624HCID 59799624, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (299 mg, 7.48 mmol) in DMF (20 ml) at 0° under argon atmosphere was added methyl 2-amino-5-hydroxybenzoate (1.25 g, 7.48 mmol) and 2-iodoacetamide (1.38 g, 7.48 mmol). The mixture was stirred at 0° for 1 hr and at r.t overnight. At 0° water was given to the reaction mixture. The product was extracted with EtOAc. The organic layers were dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography using a methylenchloride gradient to obtain the title compound (1.03 g, 64%) as off-white solid.

Workup

  1. customAt 0°
  2. extractionThe product was extracted with EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-794344eafbbc4025b50b235d5b61c7f6
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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