Methanol → 3-Amino-4-cyclobutylbenzoic acid

HRID 541449Notes

Reaction equation

HRID 541449 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]1[CH2:15][CH2:14][CH2:13]1)[C:5]([O:7]C)=[O:6].[OH-].[Na+].CO>O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]1[CH2:13][CH2:14][CH2:15]1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 68288285Methyl 3-amino-4-cyclobutylbenzoate

Product 1

HCID 682883583-Amino-4-cyclobutylbenzoic acidYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

Into around-bottom flask, was placed a solution of methyl 3-amino-4-cyclobutylbenzoate (1.00 g, 4.87 mmol, 1.00 equiv) and sodium hydroxide (compound 443.2, 800 mg, 20.0 mmol, 4.00 equiv) in a solvent mixture of methanol and H2O (20/10 mL). The resulting solution was stirred for 8 h at 20° C. After cooling to ambient temperature, the organic solvent was removed under reduced pressure. The pH of the remaining aqueous layer was adjusted to ˜4-5 with HCl (aqueous, 1 M). The resulting precipitate was then collected by filtration and dried to furnish 500 mg (54%) of the title compound as a white solid.

Workup

  1. customInto around-bottom flask, was placed
  2. temperatureAfter cooling to ambient temperature
  3. customthe organic solvent was removed under reduced pressure
  4. filtrationThe resulting precipitate was then collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-9ecc3ed04adc4e6ea389a5ed33533561
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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