Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 178492066, compound

HRID 2271102Notes

Reaction equation

HRID 2271102 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.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1.Cl.ClC1C=CC(NN)=CC=1>>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]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:30]2)=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 18329911HCID 18329911, compound

Product 1

HCID 178492066HCID 178492066, compoundYield 4%

Procedure

Following a similar procedure to that described in Example 4, except using ethyl 4-chloro-2-methyl-3-phenyl-5-pyridinecarboxylate and 4-methoxyphenylhydrazine 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) and recrystallization (CH2Cl2-MeOH-EtOAc), in 4% yield as a yellow solid; mp 300-310° C.; 1H NMR (360 MHz, DMSO-d6) δ2.25 (3H, s), 3.74 (3H, s), 6.93 (2H, d, J 9.2 Hz), 7.43 (1H, m), 7.47-7.51 (4H, m), 7.95 (21H, d, J 9.1 Hz), 8.50(1H, s), 12.34 (1H, br s); MS (ES+) m/z 332 [MH]+. Anal. found: C, 72.15; H, 4.84; N, 12.66. C20H17ClN3O2 requires: C, 72.49; H, 5.17; N, 12.68%.

Workup

  1. customafter further purification
  2. customby flash chromatography (silica gel, 5% MeOH/CH2Cl2) and recrystallization (CH2Cl2-MeOH-EtOAc)

Sources & evidence

ORD record
ord-d5c7dbe9d5794c9390e3490c36e1533d
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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