Tetrahydrofuran → Methyl 2-[2-benzylidenehydrazino]benzoate

HRID 601178

Reaction equation

HRID 601178 reaction equation
[CH:1](=[N:8][NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCC[CH2:20]1.C[Si](C=[N+]=[N-])(C)C>CO>[CH:1](=[N:8][NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([O:14][CH3:20])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 167693TrimethylsilyldiazomethaneHCID 2226872-(2-Benzylidenehydrazino)benzoic acid

Product 1

HCID 67063589Methyl 2-[2-benzylidenehydrazino]benzoateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

2-(N′-Benzylidene-hydrazino)-benzoic acid (5.0 g, 20.81 mmol) in 1:1 tetrahydrofuran and methanol (50 mL) was reacted with a solution of trimethylsilyl diazomethane in hexanes (2.0M, 12 mL, 25.0 mmol) at 0° C. for 1 hour then stirred at 25° C. for 48 hours. The solvent was removed under vacuum to give the title compound as a solid (6.00 g, 100%). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.87 (s, 3 H) 6.84 (td, J=7.54, 1.10 Hz, 1 H) 7.41 (m, 3 H) 7.54 (m, 1 H) 7.74 (m, 3 H) 7.86 (dd, J=8.09, 1.47 Hz, 1 H) 8.21 (s, 1 H) 11.02 (s, 1 H).

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-77a3df5ed4f24f969050a3b7d82fe064
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Linked notes

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