6-Phenylnicotinic acid → 6-phenylnicotinic acid N'-(4-methoxybutyryl)hydrazide

HRID 6926

Reaction equation

HRID 6926 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:17][O:18][CH2:19][CH2:20][CH2:21][C:22]([NH:24][NH2:25])=[O:23].Cl.C(N=C=NCCCN(C)C)C>N1C=CC=CC=1>[CH3:17][O:18][CH2:19][CH2:20][CH2:21][C:22]([NH:24][NH:25][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][CH:9]=1)=[O:23]

Participants

5

Reactant 3

HCID 1201186-Phenylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 865902274-Methoxybutyric acid hydrazide hydrochloride salt

Product 1

HCID 695844476-phenylnicotinic acid N'-(4-methoxybutyryl)hydrazideYield 65.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

6-Phenylnicotinic acid (5.90 g) was dissolved in pyridine (150 ml), followed by addition of 4-methoxybutyric acid hydrazide hydrochloride salt (5.99 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt (8.51 g), and stirred at 60° C. for 10 hours. After the reaction solution was cooled to ambient temperature, the solvent was evaporated under reduced pressure. The resulting residue was washed with water, to afford 6-phenylnicotinic acid N′-(4-methoxybutyryl)hydrazide as pale yellow solid (6.06 g, 65%). The physico-chemical values are as follows.

Workup

  1. temperatureAfter the reaction solution was cooled to ambient temperature
  2. customthe solvent was evaporated under reduced pressure
  3. washThe resulting residue was washed with water

Sources & evidence

ORD record
ord-e17521f35c844b38b7cd816a96b56009
Source dataset
uspto-grants-2006_08
Patent number
US07084164B2

Linked notes

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