Water → HCID 85385301, compound

HRID 1062653Notes

Reaction equation

HRID 1062653 reaction equation
Cl.[NH2:2][OH:3].[C:4]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O)#[N:5].O>N1C=CC=CC=1.C(O)C>[C:4]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[N:2][OH:3])#[N:5]

Participants

6

Reactant 3

HCID 962WaterHCID 90670m-FormylbenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 85385301HCID 85385301, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

Hydroxylamine hydrochloride (13.5 g, 194 mmol) was added to a solution of 3-cyanobenzaldehyde (25 g, 191 mmol) in 75 mL of pyridine and 75 mL of ethanol under N2. This was allowed to stir at room temperature for 14 hours. Water (50 mL) was added with vigorous stirring and an off-white solid precipitated. The solid was filtered through a glass frit and washed with another 50 mL of water. Evaporation of residual water under high vacuum gave 19.2 g (69%) of title compound. 1H NMR (CDCl3) δ: 11.61 (s, 1H); 8.21 (s, 1H); 8.00 (s, 1H); 7.96 (d, 1H), 7.85 (d, 1H), 7.61 (t, 1H).

Workup

  1. stirringwith vigorous stirring
  2. customan off-white solid precipitated
  3. filtrationThe solid was filtered through a glass frit
  4. washwashed with another 50 mL of water
  5. customEvaporation of residual water under high vacuum

Sources & evidence

ORD record
ord-e190b22a75dd4e93a19aa1e294c38107
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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