Sulfuric Acid → HCID 21957854, compound

HRID 1994063Notes

Reaction equation

HRID 1994063 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](O)([CH3:13])[CH2:9][CH:10]1[CH2:12][CH2:11]1.S(=O)(=O)(O)O.[H][H]>CO.[Pd]>[CH:10]1([CH2:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH2:1])[CH3:13])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 21957853HCID 21957853, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21957854HCID 21957854, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2.96 g (15.5 mmol) of 2-(2-aminophenyl)-1-cyclopropyl-propan-2-ol in 70 ml methanol is added 4.43 g (43.4 mmol) conc. sulfuric acid (96%). The resulting mixture is hydrogenated over 600 mg Pd/C (10%) for 20 hours at 30-35° C. After that time no more hydrogen uptake is detected. The catalyst is filtered off and the solvent removed in a water-jet vacuum. The residue is taken up in ethylacetate/water and the water phase is neutralised by the addition of sodium carbonate. The water phase is extracted twice with ethylacetate, then the combined organic phase is dried over sodium sulfate. After removal of the solvent in a water-jet vacuum, the crude amine is obtained. The obtained raw material is purified by column chromagraphy over silica gel (eluant:hexane/ether=5:1). Yield: 2.1 g 2-(2-cyclopropyl-1-methyl-ethyl)phenylamine in the form of a brown oil (1H-NMR).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent removed in a water-jet vacuum
  3. additionthe water phase is neutralised by the addition of sodium carbonate
  4. extractionThe water phase is extracted twice with ethylacetate
  5. dry with materialthe combined organic phase is dried over sodium sulfate
  6. customAfter removal of the solvent in a water-jet vacuum
  7. customthe crude amine is obtained
  8. customThe obtained raw material
  9. customis purified by column chromagraphy over silica gel (eluant:hexane/ether=5:1)

Sources & evidence

ORD record
ord-11fd246a8dff4ac7bc1ea2604e658dc7
Source dataset
uspto-grants-2010_01
Patent number
US07652059B2

Reaction notes

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