Water → HCID 23370100, compound

HRID 1901043Notes

Reaction equation

HRID 1901043 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:25])[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])=[CH:11][CH:10]=1.O>C1COCC1>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][NH:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]([CH3:25])[CH3:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 16769101HCID 16769101, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 23370100HCID 23370100, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminium hydride (0.61 g) in THF (30 ml) was added dropwise under ice-cooling a solution of N-(4-dimethylaminophenyl)-2-aminobenzamide (2.0 g) in THF (20 ml) and the mixture was heated finder reflux. To this mixture was added dropwise small portions of water, the insolubles were filtered, and the solvent was distilled off. Purification of the residue by a silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallization from ethyl acetate/hexane afforded N-(2-aminobenzyl)-N',N'-dimethyl-1,4-phenylenediamine (1.1 g, 56%).

Workup

  1. additionwas added dropwise under ice-
  2. temperaturethe mixture was heated finder
  3. temperaturereflux
  4. filtrationthe insolubles were filtered
  5. distillationthe solvent was distilled off
  6. customPurification of the residue
  7. customby a silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c1018e46f7b4416e8947a12b3f5c40f5
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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