3-Aminobenzyl alcohol → HCID 59020664, compound

HRID 2102957Notes

Reaction equation

HRID 2102957 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=O)[CH:6]=[CH:7][CH:8]=1.NC1C=C(C=CC=1)CO>CC(O)=O.Cl.C1(S)C=CC=CC=1>[N+:14]([C:11]1[CH:10]=[N:9][C:5]2[C:6]([CH:12]=1)=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=2)([O-:16])=[O:15]

Participants

6

Reactant 2

HCID 802933-Aminobenzyl alcoholHCID 72491609HCID 72491609, compound2×

Product 1

HCID 59020664HCID 59020664, compoundYield 12.6%

Reagents, catalysts & solvents 3

HCID 7969ThiophenolCatalystHCID 176Acetic AcidSolvent2×HCID 313Hydrochloric AcidSolvent2×

Procedure

3-(3-(Hydroxymethyl)phenylamino)-2-nitroacrylaldehyde (4.3 g, 19.4 mmol) was placed in 20 mL HOAc. 4.8 g of 3-aminobenzyl alcohol (4.8 g, 38.7 mmol) was dissolved in 5 mL conc HCl, then 20 mL HOAC was added to the HCl solution. This mixture was added to the reaction flask containing the 3-(3-(hydroxymethyl)phenylamino)-2-nitroacrylaldehyde in HOAc. The mixture was heated to reflux under nitrogen and after 20 min, benzene thiol (0.19 mL, 0.19 mmol) was added. The mixture was refluxed for 28 h (m/z=208.1). After allowing to cool, acid was removed under vacuum. The residue was dissolved in EtOAc/MeOH and loaded on a silica gel cartridge. Purification by column chromatography on silica gel using hexane/EtOAc (0-50%) then 10% MeOH/EtOAc as eluent gave the product (500 mg, 9%) as a brown solid.

Workup

  1. additionThis mixture was added to the reaction flask
  2. temperatureThe mixture was heated
  3. temperatureto reflux under nitrogen and after 20 min
  4. temperatureThe mixture was refluxed for 28 h (m/z=208.1)
  5. temperatureto cool
  6. customacid was removed under vacuum
  7. dissolutionThe residue was dissolved in EtOAc/MeOH
  8. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-1ffe3a9c915843aa8b0639c2c01ed769
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

Loading…