Reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11](O)(=O)[CH:12]([CH3:14])[OH:13].Cl.[OH-].[NH4+]>>[OH:13][CH:12]([C:14]1[NH:1][C:2]2[C:3]([O:9][CH3:10])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=1)[CH3:11]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
2,3-Diaminoanisole (5.88 g) and lactic acid (5.6 ml) were combined, treated with concentrated hydrochloric acid (45 ml) and heated at 100° C. for 18 h. The reaction was cooled to 0° C., neutralised with ammonium hydroxide solution and extracted with ethyl acetate (3×45 ml). The combined organic layers were dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo and the residue purified by flash chromatography on silica eluting with ethyl acetate to yield the desired product as a reddish-brown solid (4.91 g).
Workup
- temperatureThe reaction was cooled to 0° C.
- extractionextracted with ethyl acetate (3×45 ml)
- dry with materialThe combined organic layers were dried over magnesium sulphate
- filtrationfiltered
- customthe filtrate evaporated in vacuo
- customthe residue purified by flash chromatography on silica eluting with ethyl acetate
Sources & evidence
- ORD record
- ord-5b28579291ae4976832c8cc0540a95c1
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353010B1
Linked notes
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