Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 178492067, compound

HRID 2271097Notes

Reaction equation

HRID 2271097 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:15]([O:17]CC)=O)[C:13]=1[Cl:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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.C(Cl)Cl.CO.Cl.CCOCC>>[ClH:14].[CH2:1]([C:8]1[C:13]2[C:12]([C:15](=[O:17])[N:29]([C:26]3[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)[N:30]=2)=[CH:11][NH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 18329988HCID 18329988, compoundHCID 131723053HCID 131723053, compound

Product 1

HCID 178492067HCID 178492067, compoundYield 30%

Procedure

Following a similar procedure to that described in Example 4, except using ethyl 3-benzyl-4-chloro-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 trituration with CH2Cl2-Me-OH—HCl—Et2O, in 30% yield as a cream solid, mp 179-185° C.; 1H NMR (360 MHz, DMSO-d6) δ3.78 (3H, s), 4.00 (2H, m), 7.01 (2H, d, J 9.2 Hz), 7.21 (1H, t, J 7.3 Hz), 7.31 (2H, t, J 7.3 Hz), 7.41 (1H, s), 7.42 (2H, d, J 7.0 Hz), 8.05 (2H, d, J 9.2 Hz), 8.56 (1H, s), 12.52 (1H, br s); MS (ES+) m/z 332 [MH]+. Anal. found: C, 65.36; H, 4.86; N, 11.25. C20H17N3O2.HCl requires: C, 65.31; H, 4.93; N, 11.42%.

Sources & evidence

ORD record
ord-d0192d1732c748a2bd626177c9076ef3
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

Loading…