2-Aminobenzyl alcohol → HCID 178471917, compound

HRID 1647459Notes

Reaction equation

HRID 1647459 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[C:10]([C:15](=[CH:21]OCC)[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:14])[CH:11]([CH3:13])[CH3:12]>>[C:10]([C:15](=[CH:21][NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:14])[CH:11]([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 214392-Aminobenzyl alcoholHCID 54219628HCID 54219628, compound

Product 1

HCID 178471917HCID 178471917, compoundYield 77%

Procedure

2-Aminobenzyl alcohol (12.32 g, 0.1 mol) was dissolved in ethyl 2-isobutyryl-3-ethoxyacrylate (23.57 g, 0.11 mol), stirred for 2 hours at room temperature then warmed briefly to boiling. Cooling and trituration with petroleum ether gave ethyl 2-isobutyryl-3-(2-(hydroxymethyl)phenylamino)acrylate (22.29 g, 77%) as a mixture of E/Z isomers, m.p. 72°-84°.

Workup

  1. temperaturethen warmed briefly
  2. temperatureCooling

Sources & evidence

ORD record
ord-92e4b7a270fe4f5095fa79801c6ffa33
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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