Potassium Carbonate → HCID 86628200, compound

HRID 1821335Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].Cl.[O:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][Cl:22])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:22].[O:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:1][C:2]2[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=2)[CH:7]=[O:8])[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 80 °C

Procedure

5-hydroxy-2-nitrobenzaldehyde (1.00 g, 5.98 mmol) was dissolved in DMF (15.0 mL) and the solution was added with morpholinoethyl chloride hydrochloride (1.11 g, 5.98 mmol) and potassium carbonate (1.65 g, 12.0 mmol), followed by heating at 80° C. for 40 minutes. The reaction mixture was concentrated under reduced pressure, added with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (2.00 mL) and added with 4 mol/L hydrogen chloride-methanol solution (2.00 mL), followed by stirring at 0° C. The precipitated crystal was collected by filtration to obtain 5-(2-morpholinoethoxy)-2-nitrobenzaldehyde hydrochloride (1.80 g, 95%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionadded with water
extractionextracted with ethyl acetate
concentrationThe organic layer was concentrated under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate (2.00 mL)
additionadded with 4 mol/L hydrogen chloride-methanol solution (2.00 mL)
filtrationThe precipitated crystal was collected by filtration

Sources & evidence

ORD record: ord-059c9f36b870497bb4b2cf7d48d37fcb
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605272B2

Reaction notes

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