Hydrochloric Acid → HCID 9794980, compound

HRID 33561Notes

Reaction equation

HRID 33561 reaction equation
C(O[CH:5]([CH:18]([CH3:20])[CH3:19])[C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7])(=O)C.Cl.OC(C(C)C)C(C1C2C(=CC=CC=2)C=CC=1)=O.OC(C1C2C(=CC=CC=2)C=CC=1)C(=O)C(C)C.[N:56]#[C:57][NH2:58]>C(O)C>[NH2:58][C:57]1[O:7][C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)=[C:5]([CH:18]([CH3:20])[CH3:19])[N:56]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 37077282-Hydroxy-3-methyl-1-naphthalen-1-yl-butan-1-oneHCID 235936071-Hydroxy-3-methyl-1-naphthalen-1-yl-butan-2-oneHCID 597968562-Acetoxy-3-methyl-1-(naphth-1-yl)butan-1-one

Product 1

HCID 9794980HCID 9794980, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2-acetoxy-3-methyl-1-(naphth-1-yl)butan-1-one (8.4 g), IMS (200 ml) and hydrochloric acid (1M; 100 ml) were boiled under reflux for 4 hours. The mixture was cooled, evaporated in vacuo and partitioned between dichloromethane and brine. The organic layer was separated, dried with sodium sulphate, filtered and evaporated in vacuo to afford a mixture of crude 2-hydroxy-3-methyl-1-naphthalen-1-yl-butan-1-one and 1-hydroxy-3-methyl-1-naphthalen-1-yl-butan-2-one (F) (7.4 g). Cyanamide (1.3 g) and anhydrous ethanol (50 ml) were added and the resulting mixture was boiled under reflux for 96 hours. After cooling the volatiles were removed in vacuo and the residue heated at 115° C. for a further 48 hours. The mixture was cooled, triturated with chloroform (80 ml) and filtered. The filtrate was washed with water, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound (7) was obtained (0.26 g; m.p. 127-129° C.) following silica gel column chromatography of the residue in 33% ethyl acetate in petroleum ether and re-crystallisation from dichloromethane/petroleum ether.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe mixture was cooled
  3. customevaporated in vacuo
  4. custompartitioned between dichloromethane and brine
  5. customThe organic layer was separated
  6. dry with materialdried with sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto afford
  10. temperatureunder reflux for 96 hours
  11. temperatureAfter cooling the volatiles
  12. customwere removed in vacuo
  13. temperatureThe mixture was cooled
  14. customtriturated with chloroform (80 ml)
  15. filtrationfiltered
  16. washThe filtrate was washed with water
  17. dry with materialdried with sodium sulphate
  18. filtrationfiltered
  19. customevaporated in vacuo

Sources & evidence

ORD record
ord-0a8fbca072a041dca7231b7ad252d79e
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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