N-(2-Hydroxyethyl)aniline → HCID 68576987, compound

HRID 2390909Notes

Reaction equation

HRID 2390909 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C@H:6]2[O:8][CH2:7]2)=[CH:4][CH:3]=1.[NH:11]([CH2:18][CH2:19][OH:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C@@H:6]([OH:8])[CH2:7][N:11]([CH2:18][CH2:19][OH:20])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31235N-(2-Hydroxyethyl)anilineHCID 101300744-Chlorostyrene oxide, (R)-

Product 1

HCID 68576987HCID 68576987, compoundYield 49%

Conditions

Temperature
60 °C

Procedure

To (R)-4-chloro-styrene oxide (1.55 g, 10.0 mmol), 2-anilinoethanol (1.44 g, 1.05 equivalents) was added; and the mixture was stirred at 60° C. for 15 hours. The mixture was cooled to room temperature to obtain 3.38 of the reaction mixture of the title compound (chemical purity: 52.1 area %, 2-anilinoethanol: 1.5 area %, 28.4 area % of regioisomer was contaminated). The reaction mixture was purified by column chromatography (gel: silica gel, solvent: ethyl acetate/hexane=1/1), and the obtained fractions were concentrated and dried under vacuum, to obtain 1.68 g of the title compound as pale yellow oil (yield: 49%, chemical purity: 91.7 area %; 2-anilinoethanol was not detected; 4.7 area % of regioisomer was contaminated). The retention time in the chemical purity analysis method was 5.6 min.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customto obtain

Sources & evidence

ORD record
ord-ad6d49c98c5b4929a13dc46d9f1a94cc
Source dataset
uspto-grants-2012_09
Patent number
US08273883B2

Reaction notes

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