N,N-diethyl-4-formylbenzamide → HCID 54349341, compound

HRID 2258331Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N:8]2[Si](C)(C)CC[Si]2(C)C)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH:22]([C:24]1[CH:36]=[CH:35][C:27]([C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1)=[O:23]>>[NH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:22]([C:24]1[CH:36]=[CH:35][C:27]([C:28]([N:30]([CH2:31][CH3:32])[CH2:33][CH3:34])=[O:29])=[CH:26][CH:25]=1)[OH:23]

Participants

Reactant 3

HCID 10954698N,N-diethyl-4-formylbenzamide

HCID 132686651-(3-Bromophenyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane

HCID 178418339Butyllithium

Product 1

HCID 54349341HCID 54349341, compoundYield 25.2%

Procedure

The protected aniline (23.64 g, 0.101 mol) was treated with n-butyllithium (1.5M in hexane, 66 mL, 0.101 mol) and 4-formyl-N,N -diethylbenzamide (20.70 g, 0.101 mol) as in Example11. Chromatography of the crude product on silica gel (Waters Prep 500, dichloromethane:ethanol/100:1-3) gave 7.59 g (25%) of 4-(3-amino-α-hydroxybenzyl)-N,N-diethylbenzamide as a light yellow hygroscopic solid.

Sources & evidence

ORD record: ord-e7c072720f5540d3bf6f40c64ff69515
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05658908

Reaction notes

Loading…