Hydrochloric Acid → 2-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2-(4-chloro-2-methylphenyl)acetaldehyde

HRID 1748826Notes

Reaction equation

[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:3]=1[C:14]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[CH3:25])=[CH:15][O:16]C.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:3]=1[CH:14]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[CH3:25])[CH:15]=[O:16]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-(5-chloro-4-(1-(4-chloro-2-methylphenyl)-2-methoxyvinyl)-1-methyl-1H-pyrazol-3-yl)pyridine (16.6 g, 44.4 mmol) in dioxane (80 mL) was added 6 N HCl (340 mL, 2040 mmol). The mixture was heated at about 70° C. for about 10 h then allowed to cool to rt. The mixture was neutralized with a saturated aqueous NaHCO3 solution then extracted with EtOAc (2×500 mL). The combined organic layers were washed with brine (500 mL), dried with Na2SO4, filtered and concentrated in vacuo to give 2-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2-(4-chloro-2-methylphenyl)acetaldehyde (15.98 g, 100%): LC-MS (Table 1, Method g) Rt=2.48 min, m/z 360/362 (M+H)+; 1H-NMR (CDCl3, Bruker 400 MHz) δ 9.83 (s, 1H), 8.41-8.37 (m, 1H), 8.02-7.98 (m, 1H), 7.74-7.68 (m, 1H), 7.23-7.13 (m, 2H), 7.05-6.97 (m, 1H), 6.93 (d, J=8.4 Hz, 1H), 5.75 (s, 1H), 3.94 (s, 3H), 2.37 (s, 3H).

Workup

temperatureto cool to rt
extractionthen extracted with EtOAc (2×500 mL)
washThe combined organic layers were washed with brine (500 mL)
dry with materialdried with Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c1178239755e43f3b2bfc16242b8a92b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150592B2

Reaction notes

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