4-Hydroxy-3-nitrobenzoic acid → 2-Nitrophenol

In a 50 mL polystyrene cartridge, to an amino tantagel (1 g, 0.45 mmol) in DMF (15 mL) were added 4-hydroxy-3-nitrobenzoic acid (1a) (1 g, 5.46 mmol), HOBt (1 g, 7.4 mmol), and DIC (1,3-diisopropylcarbodiimide, 1 mL, 6.4 mmol). After overnight shaking, the reaction mixture was washed with DMF (20 mL, 5 times), methylene chloride, and methanol (20 mL, 5 times each). To remove any undesirable side product, DMF (5 mL) and piperidine (0.5 mL) were-added to the cartridge and allowed to shake for 1.5 h. The resin was filtered and washed with DMF. The resulting piperidine salt was removed via the addition of a 10% HCl solution (in DMF, 20 mL) to the resin that was allowed to shake for 1.5h. The mixture was then filtered, washed with DMF (20 mL, 5 times), methanol, and methylene chloride (20 mL, 5 times each) and dried by nitrogen gas flow.

1. washthe reaction mixture was washed with DMF (20 mL, 5 times), methylene chloride, and methanol (20 mL, 5 times each)
2. customTo remove any undesirable side product, DMF (5 mL) and piperidine (0.5 mL)
3. additionwere-added to the cartridge
4. waitto shake for 1.5 h
5. filtrationThe resin was filtered
6. washwashed with DMF
7. customThe resulting piperidine salt was removed via the addition of a 10% HCl solution (in DMF, 20 mL) to the resin that
8. waitto shake for 1.5h
9. filtrationThe mixture was then filtered
10. washwashed with DMF (20 mL, 5 times), methanol, and methylene chloride (20 mL, 5 times each) and
11. customdried by nitrogen gas flow

ORD record

ord-63c46d964c9344ff8f2940b17c9931e5

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060752B2