1-{3-[(Quinolin-2-yl)methoxy]phenyl}hexan-1-ol → HCID 20226648, compound

HRID 1732107Notes

Reaction equation

HRID 1732107 reaction equation
[OH:1][CH:2]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].ClC1C=C(C=CC=1)C(OO)=[O:31]>C(Cl)Cl>[OH:1][CH:2]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N+:14]=1[O-:31])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 50591-{3-[(Quinolin-2-yl)methoxy]phenyl}hexan-1-olHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 20226648HCID 20226648, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.0 g (0.015 mol) 2-[3-(1-hydroxyhexyl)phenoxymethyl]quinoline and 3.0 g (0.017 mol) m-chloroperoxybenzoic acid in 100 ml CH2Cl2 was stirred at room temperature for a period of 24 hours. The reaction mixture was extracted with dilute NaHCO3 solution, washed with water, dried over MgSO4 and concentrated to dryness under reduced pressure. The residue was triturated with large amounts of ether to obtain a solid. This solid was filtered, washed with ether and dried to give the desired compound (2 g).

Workup

  1. extractionThe reaction mixture was extracted with dilute NaHCO3 solution
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was triturated with large amounts of ether
  6. customto obtain a solid
  7. filtrationThis solid was filtered
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-38e7f46ede484771ad4cd0da699b6744
Source dataset
uspto-grants-1986_11
Patent number
US04625034

Reaction notes

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