m-Chloroperbenzoic acid → (1-Oxidoquinolin-4-yl)methanol

HRID 641802Notes

Reaction equation

HRID 641802 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][OH:12])=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[O-:21][N+:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][OH:12])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 804794-(Hydroxymethyl)quinoline

Product 1

HCID 21963888(1-Oxidoquinolin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of quinolin-4-ylmethanol (0.20 g, 1.26 mmol) dissolved in CH2Cl2 (10 mL), which was cooled to 0° C., was added m-chloroperbenzoic acid (57-86% w/w in H2O, 0.50 mg) in one portion. The reaction was allowed to slowly warm to room temperature while stirring. After 17.5 h, the resulting solid was filtered and washed with CH2Cl2 to yield (1-oxidoquinolin-4-yl)methanol as a white solid. MS (ES+): 176 [MH+].

Workup

  1. temperatureto slowly warm to room temperature
  2. filtrationthe resulting solid was filtered
  3. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-fecac15709d440be84d7a2f91114034c
Source dataset
uspto-grants-2010_04
Patent number
US07696225B2

Reaction notes

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