m-Chloroperbenzoic acid → 2-(4-Carboxy-2-chlorophenyl)-6-hydroxyquinoline 1-oxide

HRID 628898Notes

Reaction equation

HRID 628898 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[N:12]=1)[C:5]([OH:7])=[O:6].ClC1C=CC=C(C(OO)=[O:30])C=1>CC(O)=O>[C:5]([C:4]1[CH:8]=[CH:9][C:10]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=3)[N+:12]=2[O-:30])=[C:2]([Cl:1])[CH:3]=1)([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 56960912Cavosonstat2×

Product 1

HCID 569593382-(4-Carboxy-2-chlorophenyl)-6-hydroxyquinoline 1-oxideYield 37.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-chloro-4-(6-hydroxyquinolin-2-yl)benzoic acid (Compound 8) (620 mg) in HOAc (8 mL) was added 3-chloroperbenzoic acid (77% pure, 1.19 g). The resultant mixture was heated at 90° C. over 3 hour. After removal of HOAc under reduced pressure, the resultant mixture was trituated with DCM and recrystallized from EtOH/water twice to afford the desired product (245 mg) as colorless solids. 1H NMR (DMSO-d6 300 MHz TMS): δ 10.49 (1H, s), 8.43 (1H, d, J=9 Hz), 8.06 (1H, d, J=3 Hz), 8.01 (1H, dd, J=9 and 3 Hz), 7.82 (1H, d, J=6 Hz), 7.69 (1H, d, J=6 Hz), 7.47 (1H, d, J=9 Hz), 7.37 (1H, dd, J=9 and 3 Hz), 7.31 (1H, d, J=3 Hz) ppm; MS (ESI): m/z 316, [M+H+].

Workup

  1. customAfter removal of HOAc under reduced pressure
  2. customrecrystallized from EtOH/water twice

Sources & evidence

ORD record
ord-3fe64b45422445e4a3f8d9a26af11d60
Source dataset
uspto-grants-2016_04
Patent number
US09315462B2

Reaction notes

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