Clonidine → HCID 178519725, compound

HRID 2166822Notes

Reaction equation

HRID 2166822 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=1[NH:19][C:20]1[NH:21][CH2:22][CH2:23][N:24]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.CN(P(N(C)C)(N(C)C)=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:24]2[CH2:23][CH2:22][N:21]=[C:20]2[NH:19][C:13]2[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])=[O:8])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 2803ClonidineHCID 516892Sodium BicarbonateHCID 178418479HCID 178418479, compound

Product 1

HCID 178519725HCID 178519725, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

3.25 g (22.9 millimoles) of 6-hydroxy-nicotinic acid are dissolved in 600 ml of absolute tetrahydrofuran and 60 ml of absolute hexamethylphosphorotriamide, 3.8 g (22.9 millimoles) of N,N'-carbonyl-diimidazole are added and the mixture is stirred for 45 minutes at room temperature. A solution of 5.3 g (11.0 millimoles) of 2-(2',6'-dichlorophenylamino)-2-imidazoline in 100 ml of absolute tetrahydrofuran is then added dropwise and the mixture is left to stand overnight. The solvents are then stirred off under reduced pressure on a rotary evaporator, the residue is treated with 50 ml of 0.5% strength sodium bicarbonate solution and the mixture is decanted. 3.2 g of semi-crystalline, crude (6-hydroxynicotinoyl)-2-(2',6'-dichlorophenylamino)-2-imidazoline are obtained, which on recrystallization from isopropanol give a pure product of melting point 256°-258° C.

Workup

  1. waitthe mixture is left
  2. waitto stand overnight
  3. stirringThe solvents are then stirred off under reduced pressure on a rotary evaporator
  4. customthe mixture is decanted

Sources & evidence

ORD record
ord-0f76fe844c334b2b8fa822616ea40167
Source dataset
uspto-grants-1983_06
Patent number
US04389403

Reaction notes

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