Sodium Hydroxide → 3-Benzyl-4-chloroaniline

HRID 1111351Notes

Reaction equation

HRID 1111351 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:26])=[C:16]([CH:25]=1)[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.[OH-].[Na+]>CCOCC.O>[CH2:17]([C:16]1[CH:25]=[C:12]([CH:13]=[CH:14][C:15]=1[Cl:26])[NH2:11])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 10489713(5-Amino-2-chlorophenyl)(phenyl)methanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 221522153-Benzyl-4-chloroaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

6.8 g of lithium aluminium hydride, followed by 44.4 g of aluminium chloride and then 22 g of 5-amino-2-chlorobenzophenone dissolved in anhydrous ether are added in small amounts, under a nitrogen atmosphere, into 1000 ml of anhydrous ether which is cooled to 0° C. After stirring for 2 hours and under reflux, the excessive reagents are decomposed by very slowly adding 7 ml of 15% caustic soda and, finally, 21 ml of water. After filtering and washing the precipitate with 2×200 ml of ether, the organic phase is washed, dried over Na2SO4 and then evaporated to dryness under vacuum.

Workup

  1. temperatureunder reflux
  2. filtrationAfter filtering
  3. washwashing the precipitate with 2×200 ml of ether
  4. washthe organic phase is washed
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-040147399a444ba18ed3d5cb097da47b
Source dataset
uspto-grants-1990_12
Patent number
US04980349

Reaction notes

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