3-(Chloromethyl)pyridine hydrochloride → HCID 19088793, compound

HRID 1656092Notes

Reaction equation

[N:1]1([C:7]2[O:8][C:9]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[CH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30]Cl)[CH:25]=1>CN(C)C=O>[N:1]1([C:7]2[O:8][C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:30][C:26]4[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=4)=[CH:16][CH:15]=3)=[CH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Morpholinyl-6-(4-hydroxyphenyl)-4-pyrone, as prepared in Example 5, (273 mg, 1.0 mmole) was suspended in 6 ml dimethylformamide in a 25 ml one neck round bottom flask under nitrogen. The suspension was treated with sodium hydride suspension (192 mg, 4.0 mmole) and the reaction mixture was warmed to 60° C. for 40 minutes. The reaction was treated with 3-picolyl chloride hydrochloride (492 mg, 3.0 mmole) and the mixture was stirred 2 hours at 60° C. The reaction was poured into 50 ml 2N sodium hydroxide/ice and the mixture was extracted with 4×20 ml dichloromethane. The combined organics were washed with 4×25 ml 50% saturated sodium chloride and were dried over magnesium chloride. The dried organics were concentrated in vacuo to a yellow solid. The crude material was recrystallized twice from ethyl acetate to provide 229 mg (62%) of Compound 5 as a golden crystalline solid.

Workup

extractionthe mixture was extracted with 4×20 ml dichloromethane
washThe combined organics were washed with 4×25 ml 50% saturated sodium chloride
dry with materialwere dried over magnesium chloride
concentrationThe dried organics were concentrated in vacuo to a yellow solid
customThe crude material was recrystallized twice from ethyl acetate

Sources & evidence

ORD record: ord-0af532ea3636430fb07d3f35ab8daf1c
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05252735

Reaction notes

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