Diethyl Ether → 3-(3-Pyridinyl)benzoic acid hydrazide

HRID 906825Notes

Reaction equation

HRID 906825 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10](OC)=[O:11])[CH:2]=1.[NH2:17][NH2:18].C(OCC)C>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([NH:17][NH2:18])=[O:11])[CH:2]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9321HydrazineHCID 4133188Methyl 3-(3-pyridinyl)benzoate

Product 1

HCID 591273483-(3-Pyridinyl)benzoic acid hydrazideYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-(pyridin-3-yl)benzoate (190 mg, 0.89 mmol) in anhydrous methanol (1 mL) was added hydrazine (0.07 mL,). The solution was stirred at RT overnight before ethyl ether was added. The solid was filtered and washed with ethyl ether to give 67 mg (35% yield) of 3-(pyridin-3-yl)benzohydrazide as a white solid. An additional 120 mg of the product was recovered from the filtrate. (M+H)+=214.13

Workup

  1. additionwas added
  2. filtrationThe solid was filtered
  3. washwashed with ethyl ether

Sources & evidence

ORD record
ord-ed4813d52ee44a4c93424668940f0b57
Source dataset
uspto-grants-2011_09
Patent number
US08013004B2

Reaction notes

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