Methyl morpholine oxide → 4-(4-Benzylphenylamino)-6-chloroquinoline-3-carbaldehyde

HRID 1944593Notes

Reaction equation

HRID 1944593 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[N:18]=[CH:17][C:16]=2[CH2:26][OH:27])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[N:18]=[CH:17][C:16]=2[CH:26]=[O:27])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58525065(4-(4-Benzylphenylamino)-6-chloroquinolin-3-yl)methanol

Product 1

HCID 585251174-(4-Benzylphenylamino)-6-chloroquinoline-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(4-benzylphenylamino)-6-chloroquinolin-3-yl)methanol (800 mg, 2.1 mmol) in CH2Cl2 (9 mL) was added 4-Methylmorpholine N-oxide (377 mg, 3.2 mmol) and tetrapropylammonium perruthenate at room temperature and stirred for overnight. The reaction mixture was filtered and concentrated. The crude product was used without further purification. MS m/z: 373.28 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-7c318c4fa63743be9c78efaea0ab2c52
Source dataset
uspto-grants-2013_03
Patent number
US08394818B2

Reaction notes

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