m-Chloroperbenzoic acid → [4-(7-Oxido-3-phenyl-1,7-naphthyridin-2-yl)phenyl]methanol

HRID 605006Notes

Reaction equation

HRID 605006 reaction equation
[C:1]1([C:7]2[C:8]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=3)=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[N:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[O-:33][N+:12]1[CH:11]=[C:10]2[C:15]([CH:16]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]([C:17]3[CH:18]=[CH:19][C:20]([CH2:23][OH:24])=[CH:21][CH:22]=3)=[N:9]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59846130[4-(3-Phenyl-1,7-naphthyridin-2-yl)phenyl]methanol

Product 1

HCID 59846139[4-(7-Oxido-3-phenyl-1,7-naphthyridin-2-yl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of [4-(3-phenyl-1,7-naphthyridin-2-yl)phenyl]methanol (142 mg, 0.455 mmol) in chloroform (3 mL) was added a solution of m-chloroperbenzoic acid (85%, 105 mg, 0.47 mmol) in chloroform (2 mL). The reaction was stirred over night and then the solvent was removed in vacuo. The residue was digested with diethyl ether twice to remove the m-chlorobenzoic acid and give the title compound as a yellow solid. 1H-NMR (500 MHz, CDCl3): δ 9.07 (1H, s), 8.24 (1H, d, J=6.8 Hz), 8.09 (1H, s), 7.70 (1H, d, J=7.1 Hz), 7.41 (2H, d, J=8.1 Hz), 7.22-7.39 (7H, m), 4.71 (2H, s). m/e (m+1): 329.2.

Workup

  1. customthe solvent was removed in vacuo
  2. customto remove the m-chlorobenzoic acid

Sources & evidence

ORD record
ord-f3e426e616924cc5a4059ced2e349ddb
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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