Triethylamine → N-methyl-N'-(4-methyl-naphthalen-1-yl)-hydrazinecarboxylic acid tert-butyl ester

HRID 1438078Notes

Reaction equation

HRID 1438078 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:10])[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].B(O)(O)[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH3:22])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]([CH3:10])[NH:9][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH3:22])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27735114-Methyl-1-naphthaleneboronic acidHCID 37482801-Boc-1-methylhydrazine2×

Product 1

HCID 57941313N-methyl-N'-(4-methyl-naphthalen-1-yl)-hydrazinecarboxylic acid tert-butyl esterYield 9.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 450 mg, 3.1 mmol), (4-methyl-1-naphthalene)boronic acid (Aldrich; 561 mg, 3.0 mmol), copper(II) acetate (559 mg, 3.1 mmol) and triethylamine (430 μL, 3.1 mmol) in 1,2-dichloroethane (4 mL) was heated in an oil bath at 50° C. for 3 h. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 40 g column, eluting with 5% ethyl acetate/hexanes, to give N-methyl-N′-(4-methyl-naphthalen-1-yl)-hydrazinecarboxylic acid tert-butyl ester (79 mg, 9%) as a yellow solid.

Workup

  1. temperatureto cool
  2. custompurified by chromatography
  3. washeluting with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fce03723d7f544398ecf0984c318f884
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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