Ethanol → HCID 20450128, compound

HRID 358008Notes

Reaction equation

HRID 358008 reaction equation
Br.[NH2:2][C:3]1([C:14]([OH:16])=[O:15])[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:13])[CH:9]=2)[CH2:4]1.S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[NH2:2][C:3]1([C:14]([O:16][CH2:22][CH3:23])=[O:15])[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:13])[CH:9]=2)[CH2:4]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric Acid2×HCID 70471019HCID 70471019, compound

Product 1

HCID 20450128HCID 20450128, compound

Procedure

2-Amino-6-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid hydrobromide (580 mg., 2.0 mM) was suspended in dry ethanol (15 ml.). Concentrated sulphuric acid (0.05 ml.) was added and the mixture was stirred under reflux. After 24 hr. reflux, more sulphuric acid (0.05 ml.) was added and the reflux was continued for 48 hr. The mixture was evaporated in vacuo. Ether (15 ml.) and ethyl acetate (20 ml.) were added to the residue, followed by water (10 ml.). The mixture was basified with dilute sodium bicarbonate solution, and then separated. The organic phase was washed successively with water (15 ml.) and saturated brine (15 ml.). The solution was dried (Na2SO4) and evaporated in vacuo, giving ethyl 2-amino-6-hydroxy-1,2,3,4-tetrahydronapthalene-2-carboxylate, Rf 0.54 [kieselgel 60, 5:1 v/v dichloromethane/methanol].

Workup

  1. temperatureunder reflux
  2. temperaturereflux
  3. waitthe reflux was continued for 48 hr
  4. customThe mixture was evaporated in vacuo
  5. additionEther (15 ml.) and ethyl acetate (20 ml.) were added to the residue
  6. customseparated
  7. washThe organic phase was washed successively with water (15 ml.) and saturated brine (15 ml.)
  8. dry with materialThe solution was dried (Na2SO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-5aa38dc4c0e543029bdd95e97ac9cc74
Source dataset
uspto-grants-1984_08
Patent number
US04464358

Reaction notes

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