2-Methoxyethylamine → 2-(N-formyl-N-(2-methoxyethyl)amino)-4'-propoxyacetophenone

HRID 482632Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)=[O:4].[CH3:15][O:16][CH2:17][CH2:18][NH2:19].C(N(C(C)C)CC)(C)C.[C:29](OC=O)(=[O:31])C>>[CH:29]([N:19]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)=[O:4])[CH2:18][CH2:17][O:16][CH3:15])=[O:31]

Participants

Reactant 4

HCID 80182-Methoxyethylamine

HCID 75269Acetic-formic anhydride

HCID 81531Diisopropylethylamine

HCID 146173262-Bromo-1-(4-propoxyphenyl)ethan-1-one

Product 1

HCID 189809872-(N-formyl-N-(2-methoxyethyl)amino)-4'-propoxyacetophenone

Procedure

By substantially following the procedure of Example 585c using 37 g (≤140 mmole) of 2-bromo-4'-propoxyacetophenone (Example 585b), 16 g (210 mmole) of 2-methoxyethylamine, 22 g (170 mmole) of diisopropylethylamine, and 50 g of formic acetic anhydride mixture (≤350 mmole) 18.5 g of the desired compound, an oil, was obtained.

Sources & evidence

ORD record: ord-69d1a7848c5247aea76f0eff1914e3e1
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05798311

Reaction notes

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