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Hydrochloric Acid → 1-Amino-3,3-dimethylbutan-2-one hydrochloride

HRID 1855210
Notes
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Reaction equation

HRID 1855210 reaction equation
[N:1]([CH2:4][C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7])=[N+]=[N-].[ClH:11]>[Pd].CO>[ClH:11].[NH2:1][CH2:4][C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 126690681-Azido-3,3-dimethylbutan-2-one

Product 1

HCID 221479671-Amino-3,3-dimethylbutan-2-one hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 2 L three-necked round-bottom flask fitted with a mechanical stirrer were added azidopinacolone (28.6 g, 203 mmol, 1.0 equiv), methanol (1145 mL), concentrated HCl (18 mL), and 10% Pd/C (3.5 g, 50% water wet). The reaction mixture was stirred under hydrogen at 20 psi for 2 h, the mixture was filtered through a pad of Celite, and the residue rinsed with methanol (2×50 mL). The filtrate was concentrated under reduced pressure at a temperature below 40° C. The resulting wet solid was azeotroped with 2-propanol (2×100 mL), anhydrous ether (100 mL) was added, and the slurry which formed was stirred for 5 min. The solid product was collected by filtration, and the cake was washed with diethyl ether (2×30 mL) and then dried in vacuo to give aminopinacolone hydrochloride A-2.

Workup

  1. customTo a 2 L three-necked round-bottom flask fitted with a mechanical stirrer
  2. filtrationthe mixture was filtered through a pad of Celite
  3. washthe residue rinsed with methanol (2×50 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure at a temperature below 40° C
  5. customThe resulting wet solid was azeotroped with 2-propanol (2×100 mL), anhydrous ether (100 mL)
  6. additionwas added
  7. customthe slurry which formed
  8. stirringwas stirred for 5 min
  9. filtrationThe solid product was collected by filtration
  10. washthe cake was washed with diethyl ether (2×30 mL)
  11. customdried in vacuo

Sources & evidence

ORD record
ord-3f01f98f90394da0a7f09f81666b9dd5
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962855B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes