Dichloromethane → 1-(p-Chlorobenzyl)-1-[4-(quinolin-2-ylmethoxy)phenyl]hydrazine

HRID 1590715Notes

Reaction equation

HRID 1590715 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.C(Cl)Cl.[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Cl)=[CH:36][CH:35]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].O>[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][N:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[CH:18][CH:17]=2)[NH2:20])=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81531DiisopropylethylamineHCID 152250684-(Quinolin-2-ylmethoxy)phenylhydrazine

Product 1

HCID 99084021-(p-Chlorobenzyl)-1-[4-(quinolin-2-ylmethoxy)phenyl]hydrazine

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A quantity of 10 g of 4-(quinolin-2-ylmethoxy)phenylhydrazine from Step C was added to a solution of 10.5 mL of diisopropylethylamine and 150 mL of CH2Cl2. To the yellow suspension was added 9.11 g of p-chlorobenzyl chloride followed by 3.64 g of Bu4NBr and 50 mL of CH2Cl2. The reaction was stirred for approximately 24 hours. When no starting material remained, the reaction was diluted with H2O and extracted 3 times with CH2Cl2. The combined organic phase was washed once with water and dried (MgSO4), filtered and evaporated to dryness. The solid residue was dried under vacuum overnight prior to being swished in ether/methanol 90/10 to give the title compound as a pale yellow solid. m.p. 130° C.

Workup

  1. extractionextracted 3 times with CH2Cl2
  2. washThe combined organic phase was washed once with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe solid residue was dried under vacuum overnight

Sources & evidence

ORD record
ord-7f552077b3b147f9b9489e2df2696db4
Source dataset
uspto-grants-1993_04
Patent number
US05204344

Reaction notes

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