2-Aminobenzyl alcohol → HCID 178450487, compound

HRID 1534461Notes

Reaction equation

HRID 1534461 reaction equation
[C:1]([C:6](=[CH:12]OCC)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][OH:20]>>[C:1]([C:6](=[CH:12][NH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][OH:20])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 214392-Aminobenzyl alcoholHCID 3359484Ethyl 2-butyryl-3-ethoxyacrylate

Product 1

HCID 178450487HCID 178450487, compound

Procedure

A mixture of ethyl 2-butyryl-3-ethoxyacrylate (23.5 g, 0.11 mol) and 2-aminobenzyl alcohol (12.3 g, 0.1 mol) was heated to 100° for 10 minutes, then diluted with petroleum ether. On cooling, ethyl 2-butyryl-3-(2-(hydroxymethyl)phenylamino)acrylate (24.9 g, 85%) crystallized as a mixture of E/Z isomers, and was filtered off and washed with petroleum ether.

Workup

  1. temperaturewas heated to 100° for 10 minutes
  2. temperatureOn cooling
  3. customethyl 2-butyryl-3-(2-(hydroxymethyl)phenylamino)acrylate (24.9 g, 85%) crystallized as a mixture of E/Z isomers
  4. filtrationwas filtered off
  5. washwashed with petroleum ether

Sources & evidence

ORD record
ord-dd4bef6be23b444592b1f0cb638fd07c
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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