2-Amino-3-Hydroxypyridine → HCID 88417582, compound

HRID 1654836Notes

Reaction equation

HRID 1654836 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:10][C:11]1[C:16]([F:17])=[C:15]([F:18])[C:14]([F:19])=[C:13]([F:20])[C:12]=1[F:21]>ClCCl.[OH-].[Na+].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:1][C:2]1[C:7]([O:8][CH2:10][C:11]2[C:12]([F:21])=[C:13]([F:20])[C:14]([F:19])=[C:15]([F:18])[C:16]=2[F:17])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 74484Pentafluorobenzyl bromide

Product 1

HCID 88417582HCID 88417582, compoundYield 65.5%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-amino-3-hydroxypyridine (8.1 g, 73.6 mmol) in dichloromethane (65 ml) and 40% sodium hydroxide (65 ml) was added Adogen 464 (5 ml) and alpha -bromo-2,3,4,5,6-pentafluorotoluene (20 g, 81 mmol) with vigorous stirring. The mixture was stirred at room temperature for 16 hours and the resulting solid was filtered off, washed and dried to yield the title compound (14 g), m.p.130°-134° C.

Workup

  1. filtrationthe resulting solid was filtered off
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-6975467bda944fa6b3776cdf60dcec30
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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