Hydrazine hydrate (1:1) → Benzoic acid, 4-(3-aminopropoxy)-, ethyl ester

A stirred mixture of 11.8 g (0.033 mole) of 4-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]benzoic acid ethyl ester and 2.4 g of 85% hydrazine hydrate in 300 mL of ethanol was heated at reflux temperature for 3 hr. After cooling the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was treated with 450 mL of 2N hydrochloric acid and filtered. The filtrate was basified to pH 11 with potassium carbonate and the mixture was extracted twice with 200 mL portions of methylene chloride. The combined extract was washed with 200 mL of water and the solvent was evaporated under reduced pressure to give 3.8 g of oil that solidified on standing.

1. temperaturewas heated
2. temperatureat reflux temperature for 3 hr
3. temperatureAfter cooling the reaction mixture
4. filtrationwas filtered
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionThe residue was treated with 450 mL of 2N hydrochloric acid
7. filtrationfiltered
8. extractionthe mixture was extracted twice with 200 mL portions of methylene chloride
9. extractionThe combined extract
10. washwas washed with 200 mL of water
11. customthe solvent was evaporated under reduced pressure

ORD record

ord-531fdcc747f2462c9fee788ede837cb4

Source dataset

uspto-grants-1991_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05061720