4-Fluorobenzaldehyde → N-[(E)-(4-fluorophenyl)methylideneamino]-3-(1H-indol-3-yl)propanamide

HRID 422835Notes

Reaction equation

HRID 422835 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([NH:14][NH2:15])=[O:13])=[CH:2]1.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[F:16][C:17]1[CH:24]=[CH:23][C:20](/[CH:21]=[N:15]/[NH:14][C:12](=[O:13])[CH2:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 2305803-Indolepropionic acid hydrazide

Product 1

HCID 42601449N-[(E)-(4-fluorophenyl)methylideneamino]-3-(1H-indol-3-yl)propanamideYield 98.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-(1H-Indol-3-yl)-propionic acid hydrazide (0.300 g, 1 eq) and 4-fluorobenzaldehyde (0.183 g, 1 eq) in toluene (7 ml) is refluxed overnight and then evaporated to dryness, to afford 0.450 g of white product that is purified by flash chromatography using neutral alumina and eluting with 1% methanol in chloroform (0.269 g, 59% yield).

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-b1cea9f23e8b4d72ba28f470c4a15f55
Source dataset
uspto-grants-2012_01
Patent number
US08101649B2

Reaction notes

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