Hydrochloric Acid → 1-Amino-4-methylpentan-2-one hydrochloride

HRID 1670529Notes

Reaction equation

HRID 1670529 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3][C:4](=[O:17])[CH2:5][N:6]1C(=O)C2C(=CC=CC=2)C1=O.[ClH:19]>C(O)(=O)C.O>[ClH:19].[NH2:6][CH2:5][C:4](=[O:17])[CH2:3][CH:2]([CH3:18])[CH3:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70388412-(4-methyl-2-oxopentyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 137017551-Amino-4-methylpentan-2-one hydrochlorideYield 81%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Slurry 2-(4-methyl-2-oxo-pentyl)-isoindole-1,3-dione (2.8 g, 11.4 mmol) in concentrated HCl (18 mL), glacial acetic acid (16 mL) and water (13 mL). Stir the mixture at reflux for 16 h. Cool to room temperature and pour the solution onto ice (25 mL). Filter off the solids, wash the filtrate with cold water (20 mL) and concentrate in vacuo to a solid. Recrystallize the solid in ethanol (15 mL) and diethyl ether (50 mL). Decant off the solvent and dry the white paste under reduced pressure to obtain the desired intermediate as a white solid (1.4 g, 81%).

Workup

  1. temperatureat reflux for 16 h
  2. additionpour the solution onto ice (25 mL)
  3. filtrationFilter off the solids
  4. washwash the filtrate with cold water (20 mL)
  5. concentrationconcentrate in vacuo to a solid
  6. customRecrystallize the solid in ethanol (15 mL)
  7. customDecant off the solvent
  8. customdry the white paste under reduced pressure

Sources & evidence

ORD record
ord-f1bb7b21e6ea49529d86b787c1a95764
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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