Ethanol → Ethyl 6-amino-2-naphthoate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.S(Cl)(Cl)=O.[CH2:19](O)[CH3:20]>>[CH2:19]([O:13][C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH2:1])[CH:3]=2)[CH:8]=1)=[O:14])[CH3:20]Participants
4
Procedure
To a solution of 6-amino-2-naphthoic acid (1 g, 5.34 mmol) in ethanol (20 mL), is added dropwise thionyl chloride (0.622 mL, 10.7 mmol). The resulting reaction solution is heated to reflux temperature under a N2 atmosphere for 3 hours. Concentration and trituration with methanol gives 6-amino-2-naphthoic acid ethyl ester as a brown oil.
Workup
- customThe resulting reaction solution
- temperatureis heated
- temperatureto reflux temperature under a N2 atmosphere for 3 hours
- concentrationConcentration and trituration with methanol
Sources & evidence
- ORD record
- ord-565e2a72e551430dbffb475669bb60f5
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202364B2
Reaction notes
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