m-Chloroperbenzoic acid → HCID 68379690, compound

HRID 1497317Notes

Reaction equation

HRID 1497317 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]2[OH:21])=[O:13])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]2[OH:21])=[O:13])[N+:5]([O-:30])=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 602098954-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide

Product 1

HCID 68379690HCID 68379690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (0.20 g, 0.57 mmol) in 3.0 mL CH2Cl2 at room temperature was added 3-chloroperbenzoic acid (0.20 g, 1.15 mmol). The reaction mixture was stirred at room temperature for 18 h. Additional 3-chloroperbenzoic acid (0.20 g, 1.15 mmol) was added to reaction mixture and was stirred at room temperature for an additional 18 h. The reaction mixture was concentrated, and the resultant residue was subjected to silica gel chromatography eluting with 0-75% ethyl acetate in hexanes to afford 4-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide 1-oxide that gave a mass ion (ES+) of 367.1 for (81Br) for M+H+.

Workup

  1. stirringwas stirred at room temperature for an additional 18 h
  2. concentrationThe reaction mixture was concentrated
  3. washeluting with 0-75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6a7cf988cf8c48eb88ce613bcb64e3b7
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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