Picolyl chloride hydrochloride → HCID 19088785, compound

HRID 1656093Notes

Reaction equation

HRID 1656093 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]=[CH:26][C:25]=1[CH2:30]Cl>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:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=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

5

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydrideHCID 97955054H-Pyran-4-one, 2-(4-hydroxyphenyl)-6-(4-morpholinyl)-

Product 1

HCID 19088785HCID 19088785, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °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 55° C. for 40 minutes. The reaction was treated with 2-picolyl chloride hydrochloride (492 mg, 3.0 mmole) and the mixture was stirred 4 hours at 55° C. The reaction was poured into 50 ml 2N sodium hydroxide/ice and the precipitated solid was collected, washed with water and diethyl ether and was dried (188 mg). The crude material was recrystallized from ethyl acetate to give 123 mg (34%) of Compound 6 as an off-white solid.

Workup

  1. customthe precipitated solid was collected
  2. washwashed with water and diethyl ether
  3. customwas dried (188 mg)
  4. customThe crude material was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-990cd7ac578e45899f5f05c8fbf4560b
Source dataset
uspto-grants-1993_10
Patent number
US05252735

Reaction notes

Loading…