1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Amino-3-bromobenzamide

To 2-amino-3-bromobenzoic acid (0.5 g, 2.3 mmol) in DMF (5 mL) at rt were added hydroxybenzatriazole (0.46 g, 3.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.53 g, 2.8 mmol), ammonium chloride (0.5 g, 9.7 mmol), and diisopropylethylamine (1.7 ml, 9.7 mmol). The mixture was purged with N2 and stirred for 6 h. The mixture was poured into water and extracted with EtOAc (3×50 mL). The combined extracts were washed with brine (2×20 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was treated with DCM (10 mL) resulting in a precipitate which was collected by filtration and dried to afford 2-amino-3-bromobenzamide as a pale pink solid (0.42 g, 84%). LCMS (ESI) m/z 215/217 (M+H)+

1. customThe mixture was purged with N2
2. additionThe mixture was poured into water
3. extractionextracted with EtOAc (3×50 mL)
4. washThe combined extracts were washed with brine (2×20 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. additionThe residue was treated with DCM (10 mL)
9. customresulting in a precipitate which
10. filtrationwas collected by filtration
11. customdried

ORD record

ord-03bf4f65c38240c8ada9e8b2fb3c9aec

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633207B2