2-Amino-3-Hydroxypyridine → HCID 20076953, compound

HRID 1654829Notes

Reaction equation

HRID 1654829 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH2:4]Cl.[NH2:12][C:13]1[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][N:14]=1>[OH-].[Na+].ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:12][C:13]1[C:18]([O:19][CH2:4][C:3]2[C:2]([CH3:1])=[CH:9][C:8]([CH3:10])=[CH:7][C:6]=2[CH3:11])=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 741082,4,6-Trimethylbenzyl chloride

Product 1

HCID 20076953HCID 20076953, compoundYield 15.5%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2,4,6-trimethylbenzyl chloride (50 g, 0.296 mol) and 2-amino-3hydroxypyridine (29.6 g, 0.269 mol) in 40% aqueous sodium hydroxide solution (200 ml) and dichloromethane (200 ml) was treated with Adogen 464 (5 ml) and stirred vigorously at room temperature for 16 hours. The product was extracted into dichloromethane and purified by flash chromatography (silica, chloroform) to yield a solid (10.1 g, 14%), m.p. 160°-166° C.

Workup

  1. extractionThe product was extracted into dichloromethane
  2. custompurified by flash chromatography (silica, chloroform)

Sources & evidence

ORD record
ord-38f23e55a6f74435b9b7b473b9a78a4a
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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