Water → 4-(4-Aminomethylbenzyl)-nitrobenzene

HRID 723558Notes

Reaction equation

HRID 723558 reaction equation
[N:1]([CH2:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:1][CH2:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 218770044-(4-Azidomethylbenzyl)-nitrobenzene

Product 1

HCID 218767314-(4-Aminomethylbenzyl)-nitrobenzeneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-azidomethylbenzyl)-nitrobenzene (5.835 g) in tetrahydrofuran (175 mL) was treated with water (0.43 mL) and triphenylphosphine (6.45 g, 1.1 eg). The mixture was stirred at room temperature for 18 hours, and the solvent was evaporated. The residue was suspended in water, and suspension made acidic by the dropwise addition of hydrochloric acid to about pH 1, then extracted with diethyl ether (3×). The aqueous phase was made alkaline with 50% aqueous sodium hydroxide, extracted with dichloromethane (3×) to afford a crude brown oil (5.66 g). Chromatography on silica gel, eluting with dichloromethane/methanol/ammonium hydroxide, gave 4-(4-aminomethylbenzyl)-nitrobenzene (3.91 g, 79%) as a yellow solid.

Workup

  1. customthe solvent was evaporated
  2. additionsuspension made acidic by the dropwise addition of hydrochloric acid to about pH 1
  3. extractionextracted with diethyl ether (3×)
  4. extractionextracted with dichloromethane (3×)
  5. customto afford a crude brown oil (5.66 g)
  6. washChromatography on silica gel, eluting with dichloromethane/methanol/ammonium hydroxide

Sources & evidence

ORD record
ord-90c9b7e726284b54835a440f4ce5004e
Source dataset
uspto-grants-2006_11
Patent number
US07141584B2

Reaction notes

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