Phenylhydrazine → HCID 178437814, compound

HRID 2271104Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]([CH2:13][CH3:14])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21]1([NH:27][NH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.ClC1C=CC(NN)=CC=1>>[ClH:1].[CH2:13]([C:4]1[NH:5][CH:6]=[C:7]2[C:8](=[O:10])[N:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:28]=[C:2]2[C:3]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:14]

Participants

Reactant 3

HCID 7516Phenylhydrazine

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

HCID 18329957HCID 18329957, compound

Product 1

HCID 178437814HCID 178437814, compoundYield 35%

Procedure

Following a similar procedure to that described in Example 4, except using ethyl 4-chloro-2-ethyl-3-phenyl-5-pyridinecarboxylate and phenylhydrazine instead of ethyl 4-chloro-3-propyl-5-pyridinecarboxylate and 4-chlorophenylhydrazine hydrochloride, the title compound was prepared in 35% yield as a yellow solid; mp 239-247° C.; 1H NMR (500 MHz, DMSO-d6) δ1.14 (3H, t, J 7.5 Hz), 2.54 (2H, q, J 7.5 Hz), 7.12 (1H, t, J 7.4 Hz), 7.39 (2H, t, J 7.6 Hz), 7.42-7.54 (5H, m), 8.02 (2H, d, J 7.7 Hz), 8.58 (1H, s), 12.59 (1H, br s); MS (ES+) m/z 316 [MH]+; Anal. found: C, 68.03; H, 5.22; N, 11.79. C20H17N3O.HCl requires: C, 68.28; H, 5.16; N, 11.94%.

Sources & evidence

ORD record: ord-131ea0a14b3b4b9ea320b6515741ce6f
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06333336B1

Reaction notes

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