Hydrochloric Acid → Methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride

HRID 1278719Notes

Reaction equation

HRID 1278719 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:6]=[CH:7][C:8]#[N:9].[ClH:15].C[CH2:17][OH:18]>>[ClH:15].[CH3:17][O:18][C:8](=[NH:9])[CH:7]=[CH:6][C:5]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 978723-(3,4-Dimethoxyphenyl)-2-propenenitrile

Product 1

HCID 86758495Methyl-(3,4-dimethoxy)-cinnamoimidate hydrochlorideYield 60%

Procedure

A suspension of 3,4-dimethoxycinnamonitrile (10 g; 52 mmol) in EtOH (150 mL) was cooled in an ice bath. The cold mixture was then saturated with hydrogen chloride. The reaction solution was refrigerated for 18 hours. The precipitate formed was collected by filtration. The colorless solid gave 8.0 g (60% yield) of methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride which was used in the next reaction, 1H-NMR (DMSO-d6; 200 MHz) δ11.8 (broad s, 1H), 10.9 (broad s, 1H), 7.82-7.9 (d, 1H), 7.3 (d, 2H), 7.02-7.12 (d, 1H), 6.81-6.9 (d, 1H), 4.2 (s, 3H), and 3.76 (s, 3H), 3.82 ppm (s, 3H).

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe precipitate formed
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-669a1e6fc5a04274a5ce75d8dbabe723
Source dataset
uspto-grants-2002_09
Patent number
US06444694B1

Reaction notes

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