Ethanol → Ethyl 6-amino-2-naphthoate

HRID 1270764Notes

Reaction equation

HRID 1270764 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

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 27339546-Aminonaphthalene-2-carboxylic acid

Product 1

HCID 58111738Ethyl 6-amino-2-naphthoate

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

  1. customThe resulting reaction solution
  2. temperatureis heated
  3. temperatureto reflux temperature under a N2 atmosphere for 3 hours
  4. 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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