Hydrochloric Acid → HCID 22463777, compound

HRID 1067149Notes

Reaction equation

HRID 1067149 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:13]=2)[CH:8]=[C:7]([C:21]([O:23][CH2:24]C)=[O:22])[CH:6]=1)(=O)C.[OH-].[Na+].Cl.OS(O)(=O)=O>O.C(O)C.CO.C([O-])(O)=O.[Na+]>[OH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:13]=2)[CH:8]=[C:7]([C:21]([O:23][CH3:24])=[O:22])[CH:6]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21192145HCID 21192145, compound

Product 1

HCID 22463777HCID 22463777, compoundYield 51.3%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent3×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of ethyl 4-acetoxy-6-morpholino-2-naphthoate (12.0 g, 34.9 mmol) and sodium hydroxide (8.4 g, 210 mmol) in water (200 cm3) and ethanol (40 cm3) was maintained at 80-90° C. for 3 hours. The cooled solution was poured into water (750 cm3) and cautiously neutralised with HCl (2M). The resulting suspension was extracted with EtOAc.(5×100 cm3). The combined extracts were dried (Na2SO4) and evaporated to give a brown solid. This solid was dissolved in methanol (200 cm3) containing c. H2SO4 (˜3 cm3) and was refluxed for 5 hours. The cooled mixture was diluted with water (900 cm3) and aq. sat. NaHCO3 solution (100 cm 3) then extracted with EtOAc (6×50 cm3). The combined extracts were washed with aq. sat. NaHCO3 (4×100 cm3) and water (100 cm3). Removal of the dried (Na2SO4) EtOAc gave a pale brown solid which was recrystallised from EtOAc/hexane to afford methyl 4-hydroxy-6-morpholino-2-naphthoate (yield=5.14 g, theoretical yield=10.0 g, 51.2%, m.p.=231-233.5° C. (uncorrected)).

Workup

  1. extractionThe resulting suspension was extracted with EtOAc
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customevaporated
  4. customto give a brown solid
  5. additioncontaining c
  6. extractionthen extracted with EtOAc (6×50 cm3)
  7. washThe combined extracts were washed with aq. sat. NaHCO3 (4×100 cm3) and water (100 cm3)
  8. customRemoval of the
  9. dry with materialdried (Na2SO4) EtOAc
  10. customgave a pale brown solid which
  11. customwas recrystallised from EtOAc/hexane

Sources & evidence

ORD record
ord-d4e16269678c4895b472b6f5dbc64d12
Source dataset
uspto-grants-2001_06
Patent number
US06248264B1

Reaction notes

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