Sodium Carbonate → HCID 59464139, compound

HRID 1713909Notes

Reaction equation

Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH:18]1[CH2:27][CH2:26][CH:21]([C:22]([O:24][CH3:25])=[O:23])[CH2:20][CH2:19]1>CS(C)=O>[CH3:8][C:7]1[C:2]([N:18]2[CH2:27][CH2:26][CH:21]([C:22]([O:24][CH3:25])=[O:23])[CH2:20][CH2:19]2)=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-chloro-3-methyl-5-nitropyridine (1.73 g, 10.00 mmol) in DMSO (20 mL) was added sodium carbonate (5.30 g, 50.00 mmol) followed by methyl isonipecotate (1.35 mL, 10.00 mmol). The reaction mixture was heated to 60° C. for 110 minutes. The reaction mixture was left to stand at room temperature overnight. A further aliquot of methyl isonipecotate (3.33 mmol, 476 mg, 450 μL) was added and heating resumed at 60° C. for 100 mins. The reaction mixture was poured onto ice water and the suspension was filtered, washed with water (4×75 mL) and dried under vacuum to leave a yellow powder; (2.43 g, 87% yield). This was used in the next stage without further purification. 1H NMR δ 1.61-1.74 (m, 2H), 1.91-2.10 (m, 2H), 2.31 (s, 3H), 2.61-2.73 (m, 1H), 2.94-3.09 (m, 2H), 3.61 (s, 3H), 3.83-3.98 (m, 2H), 8.19 (d, 1H), 8.86 (d, 1H). MS m/e MH+ 280.18.

Workup

waitThe reaction mixture was left
temperatureheating
waitresumed at 60° C. for 100 mins
additionThe reaction mixture was poured onto ice water
filtrationthe suspension was filtered
washwashed with water (4×75 mL)
customdried under vacuum
customto leave a yellow powder
customThis was used in the next stage without further purification

Sources & evidence

ORD record: ord-f1884df2cf134c9a835c98fa350a6eca
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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