Methane → Methyl 5-amino-2-hydroxybenzoate

HRID 346235

Reaction equation

HRID 346235 reaction equation
[NH2:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.CO.B(F)(F)F.[CH3:18]COCC.C>C(Cl)Cl.O>[CH3:18][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=1[OH:11]

Participants

7

Reactant 4

HCID 297MethaneHCID 887MethanolHCID 40755-Aminosalicylic AcidHCID 8000Boron trifluoride etherate

Product 1

HCID 135127Methyl 5-amino-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 76.6 g (0.5 mole) of 5-aminosalicyclic acid in 252.0 g (8 mole) of methanol was added 150.0 g (1.06 mole) of borontrifluoride etherate (Aldrich) and the mixture was heated at reflux overnight. The reaction mixture was treated with 150 mL of water and filtered. The filtrate pH was adjusted to 8.4 with sodium bicarbonate, and the resulting solid was collected by filtration and air dried to give 43.0 g (51%) of crude title compound as a solid. A sample was dissolved in methylene chloride, treated with charcoal and filtered. The filtrate was concentrated under reduced pressure to give a solid. The solid was recrystallized from methylene chloride-petroleum ether (30°-60° C.) to give title compound as golden-brown needles, mp 95°-98° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. filtrationthe resulting solid was collected by filtration and air
  5. customdried
  6. customto give 43.0 g (51%) of crude title compound as a solid
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a solid
  10. customThe solid was recrystallized from methylene chloride-petroleum ether (30°-60° C.)

Sources & evidence

ORD record
ord-3185396ff96d4a239c19fa97a0dbbc88
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Linked notes

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