4-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde → 4-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime

HRID 1245382Notes

Reaction equation

HRID 1245382 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].CO.[CH3:9][C:10]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1>CO>[CH3:9][C:10]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[CH:29]=[CH:28][C:25]([CH:26]=[N:5][OH:6])=[CH:24][CH:23]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

4

Reactant 2

HCID 219111664-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehydeHCID 86592943HCID 86592943, compound

Product 1

HCID 738530794-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde oximeYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium methoxide/hydroxylamine hydrochloride/methanol (˜1.4 M)(10.4 mL) was added to 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde (2.0 g, 7.2 mmol) in methanol (20 mL) under a nitrogen atmosphere at room temperature. The reaction was stirred for 3 h and concentrated in vacuo to give a solid. This was triturated with water saturated KH2PO4 solution and water and dried in vacuo to give 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime (1.75 g, 83%) as an off white solid. MS found: (M+H)+=293.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a solid
  3. customThis was triturated with water saturated KH2PO4 solution and water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c1c842a0e63d494d9505388e3f9f0d02
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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