Isopropanol → HCID 15703507, compound

HRID 1905411Notes

Reaction equation

HRID 1905411 reaction equation
Br[CH2:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][CH:4]=1.[OH:16][N:17]1C(=O)C2=CC=CC=C2C1=O.[OH-].[K+].C(O)(C)C.O.NN>C(Cl)Cl.CN(C)C=O>[O:16]([CH2:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][CH:4]=1)[NH2:17]

Participants

8

Reactant 5

HCID 3776IsopropanolHCID 10665N-HydroxyphthalimideHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 11414578Tert-butyl 4-(bromomethyl)benzoate

Product 1

HCID 15703507HCID 15703507, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

15.0 Grams (0.049 mole) of tert-butyl 4-bromomethylbenzoate, 8.2 g (0.05 mole) of N-hydroxyphthalimide and 3.0 (0.054 mole) of potassium hydroxide were added to 200 ml of dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes and then an 50° C. for 30 minutes. The reaction solution was cooled with ice water and filtered to obtain crystals. The crystals were dissolved in 50 ml of methylene chloride, and to this solution was slowly added dropwise 3 ml of isopropanol containing 0.5 g (0.05 mole) of hydrazine hydrate at room temperature. After completion of the addition, the reaction solution was heated under reflux for 2 hours. The reaction solution was cooled and filtered, and the filtrate was concentrated to obtain 11.0 g of tert-butyl 4-(aminoxymethyl)benzoate.

Workup

  1. waitan 50° C. for 30 minutes
  2. filtrationfiltered
  3. customto obtain crystals
  4. additionAfter completion of the addition
  5. temperaturethe reaction solution was heated
  6. temperatureunder reflux for 2 hours
  7. temperatureThe reaction solution was cooled
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d94c7941773e4e1c960f555543ffb0e5
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

Loading…