Potassium Carbonate → Benzenecarboximidamide, N-hydroxy-3,5-dimethoxy-

HRID 59259Notes

Reaction equation

HRID 59259 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:6]#[N:7].Cl.[OH:14][NH2:15].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:14][N:15]=[C:6]([NH2:7])[C:5]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 294821-(Cyanomethyl)-3,5-dimethoxybenzeneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2731154Benzenecarboximidamide, N-hydroxy-3,5-dimethoxy-Yield 33.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared according to the procedure described in Intermediate-19 by using 3,5-dimethoxy benzonitrile (1.00 g, 6.13 mmol), hydroxyl amine HCl (0.634 g, 9.23 mmol) and potassium carbonate (2.53 g, 18.40 mmol), ethanol (20 mL) to afford 0.400 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.75 (s, 6H), 5.79 (s, 2H), 6.49 (s, 1H), 6.84 (s, 2H), 9.62 (br s, 1H); MS (m/z): 197.11 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e5e7f4936761409e869c13a5c63a49a2
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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