Dimethylformamide → HCID 22241493, compound

HRID 892210Notes

Reaction equation

HRID 892210 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.Cl.[OH:15][CH2:16][C:17]1[N:18]=[CH:19][NH:20][CH:21]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][N:18]1[C:17]([CH2:16][OH:15])=[CH:21][N:20]=[CH:19]1.[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][N:20]1[CH:21]=[C:17]([CH2:16][OH:15])[N:18]=[CH:19]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 178418488HCID 178418488, compound

Product 2

HCID 22241493HCID 22241493, compoundHCID 22241495HCID 22241495, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloromethyl-quinoline hydrochloride (2.24 g, 10.5 mmol), 4-(hydroxymethyl)-imidazole hydrochloride (1.35 g, 10 mmol) and K2CO3 (4.2 g, 30 mmol) are dissolved/suspended in anhyd. DMF (20 mL) and heated to 100° C. with rapid stirring overnight. The reaction is cooled to r.t. and poured into water (400 mL) and extracted with chloroform (3×150 mL). The organic fractions are pooled and washed with brine (2×200 mL), dried over MgSO4, filtered and reduced under vacuum to an oil. The crude material is purified by flash chromatography (silica, 5% methanol in dichloromethane) to give (3-quinolin-2-ylmethyl-3H-imidazol-4-yl)-methanol and (1-quinolin-2-ylmethyl-1H-imidazol-4-yl)-methanol in a 2:3 ratio. The identity of each regioisomer was determined by NMR NOE experiments. MS (ESI) 240 (M+H)+ found for both regioisomers.

Workup

  1. extractionextracted with chloroform (3×150 mL)
  2. washwashed with brine (2×200 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe crude material is purified by flash chromatography (silica, 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c2e99b9b8a6e40fba1be715f1d49d7e8
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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