Hydrochloric Acid → Ethyl 2-(2-methoxyphenyl)acetimidate

HRID 42264Notes

Reaction equation

HRID 42264 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].Cl.[CH2:13]([OH:15])[CH3:14]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10](=[NH:11])[O:15][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 81496(2-Methoxyphenyl)acetonitrile

Product 1

HCID 23025455Ethyl 2-(2-methoxyphenyl)acetimidate

Procedure

Into a 500 mL round-bottomed flask was added 2-(2-methoxyphenyl)acetonitrile (50.45 g, 343 mmol) in ethanol (101 mL). HCl (10.42 mL, 343 mmol) gas was bubbled through the suspension for 15 minutes. The HCl bubbler was removed and the reaction was stirred at ambient temperature for 48 hours. The reaction was diluted with 200 mL ether, and the suspension was filtered. The collected solid was washed with ether and dried under vacuum to provide the title compound as the hydrochloride salt. MS (DCI+) m/e 194.0 (M+H)+.

Workup

  1. customThe HCl bubbler was removed
  2. additionThe reaction was diluted with 200 mL ether
  3. filtrationthe suspension was filtered
  4. washThe collected solid was washed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-60df3e3b2ff341b187111c1f4d18894b
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Reaction notes

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