4-Cyanobenzaldehyde → HCID 140033, compound

HRID 1385910Notes

Reaction equation

HRID 1385910 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].Cl.[CH3:12][NH:13][OH:14].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N+:13]([CH3:12])[O-:14])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 77906N-methylhydroxylamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 140033HCID 140033, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-cyanobenzaldehyde (3.3 g, 25.2 mmol), N-methylhydroxyamine hydrogen chloride and sodium bicarbonate (4.23 g, 50.4 mmol) in dry methylene chloride (80 ml) was stirred at rt for 5 hrs. The solid portion was filtered off and the filtrate was concentrated to give the product as white solid (98% yield). 1H NMR (300 MHz, CDCl3) δ3.94(s, 3H), 7.46(s, 1H), 7.72(d, J=8 Hz, 2H), 8.32(d, J=8 Hz, 2H). MS (NH3-CI) Calc. for (M+1)+: 161. Found: 161.

Workup

  1. filtrationThe solid portion was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-df06f1989cd74ba7a8cb868b95f3a5a9
Source dataset
uspto-grants-2001_07
Patent number
US06265400B1

Reaction notes

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