Hydrazine hydrate (1:1) → 2-(Methoxymethyl)-2,3-dihydro-1H-inden-2-amine

HRID 19728Notes

Reaction equation

HRID 19728 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([N:13]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1.O.NN>C(O)C>[CH3:1][O:2][CH2:3][C:4]1([NH2:13])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)3×HCID 685632312-(2-Methoxymethylindan-2-yl)-isoindole-1,3-dione

Product 1

HCID 534076272-(Methoxymethyl)-2,3-dihydro-1H-inden-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(2-methoxymethylindan-2-yl)-isoindole-1,3-dione (0.30 g, 0.976 mmol) and hydrazine hydrate (47 μl, 0.976 mmol) in 95% ethanol (15 ml) is heated to reflux for 45 hours. Further hydrazine hydrate (9.4 μl, 0.976 mmol) is added and the reaction refluxed for an additional 16 hours, followed by addition of a final portion of hydrazine hydrate (9.4 μl, 0.976 mmol) and a further 16 hours reflux. After cooling, the resultant suspension is filtered and the filter cake washed with ethanol. The combined filtrate and washings are evaporated and triturated with ether to afford 2-methoxymethylindan-2-ylamine, MH+178.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 45 hours
  3. temperaturethe reaction refluxed for an additional 16 hours
  4. temperaturea further 16 hours reflux
  5. temperatureAfter cooling
  6. filtrationthe resultant suspension is filtered
  7. washthe filter cake washed with ethanol
  8. customThe combined filtrate and washings are evaporated
  9. customtriturated with ether

Sources & evidence

ORD record
ord-6701d69aee314211944330f445d96ad7
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

Loading…