Potassium Carbonate → N-(2-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine

HRID 1013040Notes

Reaction equation

HRID 1013040 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.Cl.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1)[NH2:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 769652-Bromobenzyl bromideHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 58948771N-(2-Bromobenzyl)-N-(4-methoxyphenyl)hydrazineYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 2-bromobenzyl bromide (500 mg, 2.00 mmol) and 4-methoxyphenylhydrazine hydrochloride (348 mg, 2.00 mmol) in N,N-dimethylformamide (8 mL) was added potassium carbonate (1.38 g, 10.0 mmol). The reaction mixture was heated at 90° C. for 4 hours. The reaction was partitioned between water and methylene chloride. The methylene chloride was dried (MgSO4), concentrated and purified by SiO2 chromatography with 10-50% ethyl acetate/hexanes to give 298 mg of the title compound. LC-MS (C14H18BrN2O calculated 306) m/z 307 (M+H).

Workup

  1. customThe reaction was partitioned between water and methylene chloride
  2. dry with materialThe methylene chloride was dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by SiO2 chromatography with 10-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2250a1a107c948a6a17e7e83cca6eed1
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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