Acetic Acid → 1-(2,3-dihydro-1H-inden-2-yl)ethan-1-amine

HRID 83669Notes

Reaction equation

HRID 83669 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10](=O)[CH3:11].[NH3:13].[BH4-].[Na+].C(O)(=O)C>CO>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH:10]([NH2:13])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 111163412-Acetylindane

Product 1

HCID 120903721-(2,3-dihydro-1H-inden-2-yl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2,3-dihydro-1H-inden-2-yl)ethanone (44 mg, 0.275 mmol) was dissolved in methanol (2 mL), and 7 M methanolic ammonia was added (1 mL, 7 mmol). This was allowed to stir at rt for 4 h, at which time sodium borohydride (31 mg, 0.824 mmol) and a catalytic drop of glacial acetic acid was added. Stirring continued for 14 h at rt, after which time the solvent was removed in vacuo. The residue was taken up in ethyl acetate and washed with a small amount of 10% aqueous sodium carbonate, dried with magnesium sulfate, and concentrated. The residue was then taken on in subsequent reactions without further purification or characterization.

Workup

  1. customafter which time the solvent was removed in vacuo
  2. washwashed with a small amount of 10% aqueous sodium carbonate
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was then taken on in subsequent reactions without further purification or characterization

Sources & evidence

ORD record
ord-0660419ae2d9408b8861ed03c5800d81
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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