Acetic Anhydride → HCID 22614793, compound

HRID 842603Notes

Reaction equation

HRID 842603 reaction equation
[NH2:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([NH:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 226147952-Amino-3-hydroxy-4-methoxybenzaldehyde

Product 1

HCID 22614793HCID 22614793, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

2-Amino-3-hydroxy-4-methoxybenzaldehyde (20.0 g, 0.12 mol) [M. Grossa, F. Wessely Monatsh. Chem. 1966, 97, 1384-1390] is dissolved at RT in a mixture of pyridine (250 ml) and acetic anhydride (250 ml). The solution is warmed to 60° C. and stirred for 1.5 h. The reaction solution is then poured onto a mixture of ice and half-concentrated aqueous NaCI solution (1:1), extracted with ethyl acetate (5 times), dried over MgSO4, filtered off and concentrated in vacuo. The title compound is obtained as a slightly yellow solid (12.5 g) after silica gel chromatography [petroleum ether/ethyl acetate (7:3)]. TLC, silica gel (glass plates), petroleum ether/ethyl acetate (7:3), Rf=0.23.

Workup

  1. extractionextracted with ethyl acetate (5 times)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered off
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-979d7c92a53a4c5da91bfff4b12c23d3
Source dataset
uspto-grants-2002_04
Patent number
US06376485B1

Reaction notes

Loading…