2-Aminophenol → N-(2-Hydroxyphenyl)benzamide

To a mixture of 2-aminophenol (1.09 g, 10.0 mmol) and triethylamine (2.09 mL, 15.0 mmol) in THF (20 mL) was added benzoyl chloride (1.16 mL, 10.0 mmol) in THF (4 mL) dropwise over a period of 5 min at 0° C. After addition was complete the reaction mixture was kept on stirring at room temperature for overnight. The reaction mixture was concentrated at reduced pressure. The residue was taken up in methanol, aqueous sodium hydroxide (NaOH) (8M, 5 mL) was added. After 5 min the pH of the reaction mixture was adjusted to 7.0 by addition of glacial acetic acid and concentrated in vacuo. The reaction mixture was dissolved in dichloromethane (CH2Cl2), washed successively with 1M aqueous hydrochloric acid (HCl), saturated aqueous sodium hydrogen carbonate (NaHCO3). The organic layer was dried over sodium sulphate (Na2SO4), filtered and concentrated to give desired product (1.69 g).

1. additionAfter addition
2. concentrationThe reaction mixture was concentrated at reduced pressure
3. additionaqueous sodium hydroxide (NaOH) (8M, 5 mL) was added
4. additionAfter 5 min the pH of the reaction mixture was adjusted to 7.0 by addition of glacial acetic acid
5. concentrationconcentrated in vacuo
6. dissolutionThe reaction mixture was dissolved in dichloromethane (CH2Cl2)
7. washwashed successively with 1M aqueous hydrochloric acid (HCl), saturated aqueous sodium hydrogen carbonate (NaHCO3)
8. dry with materialThe organic layer was dried over sodium sulphate (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-566db7b5ffb04817b5fb5b535ecbe3b9

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07186718B2