Ethylenediamine → HCID 58056094, compound

A suspension of 3-methoxy-4-nitro-benzoic acid (1.5 g, 7.61 mmol) in thionyl chloride (20 mL) and N,N-dimethylformamide (2 drops) was heated at reflux for 2 hours. The solvent was then evaporated under reduced pressure to give a light yellow solid. A portion of this residue (3.8 mmol) was dissolved in acetone (previously dried over anhydrous sodium sulfate) (20 mL) and cooled in an ice bath. Then a solution of ethylendiamine (0.46 mL, 7.62 mmol) in water (10 mL) was added at 0° C. and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between water and ethyl acetate; the aqueous phase was separated and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified on a silica gel plug (EtOAc/MeOH, 100/0 to 98/2) to afford 0.42 g (46% 2 steps yield) of N-(2-hydroxy-ethyl)-3-methoxy-4-nitro-benzamide.

1. temperaturewas heated
2. temperatureat reflux for 2 hours
3. customThe solvent was then evaporated under reduced pressure
4. customto give a light yellow solid
5. dry with materialpreviously dried over anhydrous sodium sulfate) (20 mL)
6. temperaturecooled in an ice bath
7. customThe reaction mixture was partitioned between water and ethyl acetate
8. customthe aqueous phase was separated
9. extractionextracted twice with ethyl acetate
10. washThe combined organic extracts were washed with brine
11. dry with materialdried over anhydrous sodium sulfate
12. filtrationfiltered
13. customevaporated under reduced pressure
14. customThe crude residue was purified on a silica gel plug (EtOAc/MeOH, 100/0 to 98/2)

ORD record

ord-dcd3b9364ade4a5d96044673d0f7d923

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255110B2