Water → 6-Chloroquinoline-2-carbaldehydeoxime

HRID 2053809Notes

Reaction equation

HRID 2053809 reaction equation
Cl.[NH2:2][OH:3].C(N(CC)CC)C.[Cl:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH:22]=O)[CH:16]=[CH:15]2.O>CN(C=O)C.C(O)C>[Cl:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH:22]=[N:2][OH:3])[CH:16]=[CH:15]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2712836-Chloroquinoline-2-carbaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 1363477776-Chloroquinoline-2-carbaldehydeoxime

Reagents, catalysts & solvents 1

HCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

0.33 g (4.8 mmol) of hydroxylamine hydrochloride and then 0.9 mL (4.6 mmol) of triethylamine are added to a solution of 0.83 g (4.34 mmol) of 6-chloroquinoline-2-carbaldehyde in 20 mL of DMF/ethanol (v/v 1:1). The reaction mixture is stirred for 16 hours at ambient temperature; then it is poured into water. The precipitated solid is filtered off and dried. Yield: 0.79 g (88% of theory); Rf value: 0.73 (silica gel; dichloromethane/methanol=9:1); C10H7ClN2O (206.63); mass spectrum: (M+H)+=407/209 (chlorine isotope).

Workup

  1. filtrationThe precipitated solid is filtered off
  2. customdried

Sources & evidence

ORD record
ord-15f2c4504c454b1999dabe922d921dd1
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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