Sulfuric Acid → 2-Benzylindan-2-ylamine

HRID 19729Notes

Reaction equation

HRID 19729 reaction equation
[CH2:1]([C:8]1([NH:18]C(=O)C(F)(F)F)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O>C(O)(=O)C>[CH2:1]([C:8]1([NH2:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric Acid2×HCID 86611441HCID 86611441, compound

Product 1

HCID 438094522-Benzylindan-2-ylamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of N-(2-benzyl-1-oxoindan-2-yl)-2,2,2-trifluoroacetamide (0.200 g, 0.60 mmol), 10% Pdl/C (50 mg) and concentrated H2SO4 (30 μl) in acetic acid (13.3 ml) is hydrogenated at 0.35 bar for 1 hour. Further concentrated H2SO4 (10 μl) is added and the hydrogenation is continued for 16 hours. The reaction is filtered, the filtrate is evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase is basified to pH 11 with 1 M aqueous NaOH and extracted with ethyl acetate. The organic extract is washed with brine, dried (MgSO4) and evaporated to afford 2-benzylindan-2-ylamine, MH+ 224.

Workup

  1. waitthe hydrogenation is continued for 16 hours
  2. filtrationThe reaction is filtered
  3. customthe filtrate is evaporated
  4. customthe residue partitioned between ethyl acetate and water
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. washis washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-28b64453bc6e4d1bb7dc0ff62a5c9670
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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