Sodium Hydroxide → HCID 58962952, compound

HRID 917535Notes

Reaction equation

HRID 917535 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH2:12][N:13]=[N+]=[N-])[CH:6]=1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[CH2:12][NH2:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58962909HCID 58962909, compound

Product 1

HCID 58962952HCID 58962952, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The solution of 3.50 g of 1,3-bis(azidomethyl)-5-chlorobenzene in THF (20 mL) was added slowly to the LAH (1.33 g, 35.0 mmol) suspension in THF at 0° C. The resulting reaction mixture was stirred at RT for 1 hr. and then at reflux for another hour. Slow addition of 2 mL of 5% NaOH solution resulted a precipitate, which was removed by filtration. The product on solid was rinsed off with THF. The solvent was evaporated in vacuo to yield 2.60 g of 3-(aminomethyl)-5-chlorobenzylamine. 1H NMR (500 MHz, CD3OD) δ 7.25 (s, 2 H), 7.21 (s, 1 H), 3.76 (s, 4 H).

Workup

  1. customThe resulting reaction mixture
  2. temperatureand then at reflux for another hour
  3. customresulted a precipitate, which
  4. customwas removed by filtration
  5. washThe product on solid was rinsed off with THF
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5d5b4c4de05c4e5eafca1a86475073c5
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

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