2-Amino-2-methyl-1-propanol → HCID 21529153, compound

HRID 1658323Notes

Reaction equation

HRID 1658323 reaction equation
[Br:1][C:2]1[C:3]([C:8](Cl)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.BrC1C(C(O)=O)=NC=CC=1.S(Cl)(Cl)=O.[NH2:25][C:26]([CH3:30])([CH3:29])[CH2:27]O.[OH-].[Na+]>ClCCl>[Br:1][C:2]1[C:3]([C:8]2[O:9][CH2:27][C:26]([CH3:30])([CH3:29])[N:25]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 118072-Amino-2-methyl-1-propanolHCID 14798Sodium HydroxideHCID 24386Thionyl Chloride2×HCID 20501293-Bromopyridine-2-carboxylic AcidHCID 21529155HCID 21529155, compound

Product 1

HCID 21529153HCID 21529153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.0 g. of 3-bromopicolinoyl chloride (prepared by refluxing 3-bromopicolinic acid with thionyl chloride by the procedure of Example 2) in 25 ml. of dichloromethane is added to a solution of 3.9 g. of 2-amino-2-methylpropanol in 25 ml. of dichloromethane at 0°C. The resulting hydroxyalkylpicolinamide is cyclized by refluxing with thionyl chloride by the method of Leffler and Adams, J. Am. Chem. Soc. 59:2252 (1937) and the resulting hydrochloride salt is neutralized with aqueous sodium hydroxide solution to give 3-bromo-2-(4,4-dimethyl-2-oxazolinyl)pyridine.

Workup

  1. customat 0°C

Sources & evidence

ORD record
ord-bece9bcbd47b4c35b2574c8a19a98969
Source dataset
uspto-grants-1976_06
Patent number
US03963733

Reaction notes

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