Water → 2,3-Dihydro-1H-indene-1,3-diamine

HRID 264347Notes

Reaction equation

HRID 264347 reaction equation
[C:1]1(=[N:12]O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[N:10]O)[CH2:2]1.[Na].O>C(O)C>[NH2:10][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:1]([NH2:12])[CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 5360545Sodium2×HCID 135494888HCID 135494888, compound

Product 1

HCID 190367312,3-Dihydro-1H-indene-1,3-diamineYield 69.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 20 g of a 1,3-indandione dioxime in 2 L of absolute ethanol was cautiously added 160 g of sodium in portions during 1 hr (at such a rate to maintain reflux). After disappearance of the sodium, 300 mL of water was slowly added and the solution concentrated in vacuo to remove most of the ethanol. The resulting solution was acidified with conc. hydrochloric acid to pH 1-2 followed by extraction with methylene chloride to recover unreacted started material. The aqueous layer was basified with 10% sodium hydroxide to pH 12 and extracted with methylene chloride which gave 11.7 grams of crude 1,3-diaminoindan upon solvent removal in vacuo. Purification of this material by flash column chromatography eluting with 95% ethanol/ammonium hydroxide (400:16) gave 8.75 g of the title compound as an approximately 60/40 mixture of cis to trans isomers.

Workup

  1. customduring 1 hr
  2. temperatureto maintain
  3. temperaturereflux)
  4. concentrationthe solution concentrated in vacuo
  5. customto remove most of the ethanol
  6. extractionfollowed by extraction with methylene chloride
  7. customto recover unreacted
  8. extractionextracted with methylene chloride which

Sources & evidence

ORD record
ord-fb42257ab6bf4776862ece955c04765c
Source dataset
uspto-grants-1997_07
Patent number
US05646188

Reaction notes

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