Methanol → Methyl 4-(dimethylamino)-2-hydroxybenzoate

HRID 644157Notes

Reaction equation

HRID 644157 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([N:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14]O.S(Cl)(Cl)=O>CCOCC>[OH:1][C:2]1[CH:10]=[C:9]([N:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 899784-(Dimethylamino)salicylic acid

Product 1

HCID 21014871Methyl 4-(dimethylamino)-2-hydroxybenzoateYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-hydroxy-4-(N,N-dimethylamino)benzoic acid (9.05 g, 50 mmol) and MeOH (100 mL) at 0° C. was added thionyl chloride (5.34 mL, 75 mmol) dropwise. The reaction was warmed to room temperature and refluxed for 14 hours. After cooling, ether was added to the mixture and the reaction was carefully quenched with satd NaHCO3. The mixture was diluted with ether (200 mL) and partitioned. The organic layer was dried over MgSO4 and the crude product was adsorbed onto silica gel. The crude product was chromatographed on silica gel (5% CH2Cl2/hexane to 25% CH2Cl2/hexane) and triturated with ether/hexane to give the desired product as a white solid (7.1 g, 73%).

Workup

  1. temperaturerefluxed for 14 hours
  2. temperatureAfter cooling
  3. customthe reaction was carefully quenched with satd NaHCO3
  4. additionThe mixture was diluted with ether (200 mL)
  5. custompartitioned
  6. dry with materialThe organic layer was dried over MgSO4
  7. customThe crude product was chromatographed on silica gel (5% CH2Cl2/hexane to 25% CH2Cl2/hexane)
  8. customtriturated with ether/hexane

Sources & evidence

ORD record
ord-c7b667a225d04460b2a5ab5d2dcee325
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

Loading…