Chlorosuccinimide → 8-Chloro-2-methylquinolin-7-ol

HRID 1920680Notes

Reaction equation

HRID 1920680 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:20])C(=O)C1>ClCCl.C(Cl)(Cl)Cl.[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[Cl:20][C:11]1[C:2]([OH:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]=[C:8]([CH3:12])[CH:7]=[CH:6]2

Participants

6

Reactant 2

HCID 31398ChlorosuccinimideHCID 1354519692-Methylquinolin-7-ol

Product 1

HCID 1358589748-Chloro-2-methylquinolin-7-olYield 55%

Reagents, catalysts & solvents 3

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Referring to FIG. 19, under a nitrogen atmosphere, 7-hydroxyquinaldine (4, 0.39 g, 2.452 mmol) was added to a solution of NCS (0.3283 g, 2.459 mmol) and zirconium chloride (0.0285 g, 0.122 mmol) in dichloromethane (35 mL). After stirring for 23 h, the solution was diluted with chloroform and washed successively with saturated sodium carbonate solution, water, and brine. The solvent was evaporated to give a brown residue, which was purified by column chromatography (1:3 EtOAc/hexane) to yield 5c (0.2612 g, 1.349 mmol, 55%) as an oily yellow residue: 1H NMR (CDCl3) δ 8.00 (1H, d, J=8.0 Hz), 7.64 (1H, d, J=9.2 Hz), 7.28 (1H, d, J=8.0 Hz), 7.23, (1H, d, J=8.4 Hz), 2.80 (3H, s); 13C NMR (CDCl3) δ 160.6, 152.8, 144.9, 136.6, 127.5, 122.7, 120.7, 117.0, 114.6, 25.9; FTIR (neat) 2926, 1619, 1509, 1437, 1343, 1267, 1215, 1141, 1002, 835, 750 cm−1; MS (ESI) m/z calculated for (C10H8ClNO+H)+ 194 (35Cl) and 196 (37Cl), found 194 (35Cl) and 196 (37Cl); HRMS (ESI) m/z calculated for (C10H8ClNO+H)+ 194.0373 (35Cl) and 196.0343 (37Cl), found 194.0362 (35Cl) and 196.0333 (37Cl).

Workup

  1. washwashed successively with saturated sodium carbonate solution, water, and brine
  2. customThe solvent was evaporated
  3. customto give a brown residue, which
  4. customwas purified by column chromatography (1:3 EtOAc/hexane)

Sources & evidence

ORD record
ord-6ed7c1f11a5645ed910324955077d42c
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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