Formic Acid → HCID 55263543, compound

4-Amino-3-nitrophenol (36 g, 234 mmol) was split into 3 batches, approximately 12 g each. Each batch was dissolved in 150 mL of tetrahydrofuran and heated with 10 mL of 96% formic acid at 95 degrees Centigrade for 4 hours. The 3 batches were combined and concentrated. As the reactions had only proceeded ˜10% to completion, the reaction mixture was dissolved in 100 mL of 96% formic acid and heated at 110 degrees Centigrade. After 30 minutes, a precipitate began to form and 150 mL of tetrahydrofuran was added to ensure good stirring. The reaction was heated at 110 degrees Centigrade for 15 hours. The reaction was concentrated and the residue was diluted with water. The resulting solid was collected by filtration. The solid was washed three times with water and then dried in a vacuum oven at 110 degrees Centigrade for approximately 18 hours to give 40.4 g of (4-hydroxy-2-nitrophenyl)formamide. (M-1) 181.0, 1.48 min (LC/MS method B)

1. concentrationconcentrated
2. dissolutionthe reaction mixture was dissolved in 100 mL of 96% formic acid
3. temperatureheated at 110 degrees Centigrade
4. customto form
5. temperatureThe reaction was heated at 110 degrees Centigrade for 15 hours
6. concentrationThe reaction was concentrated
7. additionthe residue was diluted with water
8. filtrationThe resulting solid was collected by filtration
9. washThe solid was washed three times with water
10. customdried in a vacuum oven at 110 degrees Centigrade for approximately 18 hours

ORD record

ord-2c3015c6a6c94b6dabc2d48c9bc87f49

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07939528B2