Dimethyl Sulfoxide → HCID 18008060, compound

HRID 2117225Notes

Reaction equation

HRID 2117225 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].CS(C)=O>O>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 119282-ChloroquinolineHCID 258684-Amino-1-butanol

Product 1

HCID 18008060HCID 18008060, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloroquinoline (3.26 g, 20 mmol) and 4-amino-1-butanol are dissolved in anhyd. DMSO (10 mL) and heated to 140° C. for 4 hrs. The reaction is cooled to r.t., poured into water (250 mL) and extracted with ethyl acetate (3×100 mL). The organic fractions are pooled and washed with brine (3×150 mL), dried over MgSO4, filtered and reduced under vacuum to dryness. The crude material is purified by flash chromatography (silica, 7% methanol in dichloromethane) to give the title compound. MS (ESI) 217 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washwashed with brine (3×150 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe crude material is purified by flash chromatography (silica, 7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c4f419bd3a7d4d9fa9155f98103007b4
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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