4-Fluorophenylhydrazine hydrochloride → HCID 178433650, compound

HRID 2271103Notes

Reaction equation

HRID 2271103 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]([CH3:13])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1.Cl.ClC1C=CC(NN)=CC=1>>[F:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:8](=[O:10])[C:7]3=[CH:6][NH:5][C:4]([CH3:13])=[C:3]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:2]3=[N:29]2)=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 18329911HCID 18329911, compound

Product 1

HCID 178433650HCID 178433650, compoundYield 19%

Procedure

Following a similar procedure to that described in Example 4, except using ethyl 4-chloro-2-methyl-3-phenyl-5-pyridinecarboxylate and 4-fluorophenylhydrazine hydrochloride instead of ethyl 4-chloro-3-propyl-5-pyridinecarboxylate and 4-chlorophenylhydrazine hydrochloride, the title compound was prepared, after further purification by flash chromatography (silica gel, 5% MeOH/CH2Cl2), in 19% yield as a yellow solid; mp 303-317° C. (CH2Cl2-MeOH-EtOAc); 1H NMR (360 MHz, DMSO-d6) δ2.25 (3H, s), 7.20 (2H, t, J 9.0 Hz), 7.42 (1H, m), 7.50-7.51 (4H, m), 8.09 (2H, dd, J 9.2, J′5.2 Hz), 8.55 (1H, d), 12.43 (1H, br s); MS (ES+) m/z 320 [MH]+. Anal. found: C, 69.91; H, 4.15; N, 13.25. C19H14FN3Oe.0.3H2O requires: C, 70.27; H, 4.53; N, 12.94%.

Workup

  1. customafter further purification by flash chromatography (silica gel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7c2026e1e9464e73a6c407d048b08202
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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