Hydrochloric Acid → 4-(4-Chlorobenzyl)aniline

HRID 36722Notes

Reaction equation

HRID 36722 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.O.Cl.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[CH:16][CH:15]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 8857Ethyl AcetateHCID 35287064-Amino-4'-chlorobenzophenone

Product 1

HCID 2828554-(4-Chlorobenzyl)anilineYield 75.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4.27 g (18.4 mmols) of 4-amino-4' chloro-benzophenone and 8.54 g of zinc amalgam in 80 ml of toluene containing 4 ml of water was heated to reflux. 1 ml of concentrated hydrochloric acid were added over 90 minutes. After 22 hours, the mixture was allowed to cool to room temperature and 100 ml of ethyl acetate and 2×100 ml of water were added. The layers were separated and the aqueous phase was extracted with 50 ml of ethyl acetate. The combined organics were washed twice with 100 ml of water and 50 ml of brine, dried over MgSO4, filtered and evaporated to obtain 3.03 g of orange oil. Flash chromatography (20-35% ethyl acetate/pet ether eluent) yielded the above mentioned product as an orange liquid 915 mg (24.6% yield). 1H nmr (CDCl3) δ3.58 (2H, br s) , 3.82 (2H, s), 6.62 (2H, d), 6.94 (2H, d), 7.08 (2H, d), 7.22 (2H, d)

Workup

  1. temperaturewas heated to reflux
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with 50 ml of ethyl acetate
  4. washThe combined organics were washed twice with 100 ml of water and 50 ml of brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3fb56c4328cf4a9186492b7af4000546
Source dataset
uspto-grants-1995_05
Patent number
US05416112

Reaction notes

Loading…