Potassium Carbonate → HCID 66673454, compound

HRID 422192

Reaction equation

HRID 422192 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.Cl[C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+].CC(N(C)C)=O>C1(C)C=CC=CC=1>[O:12]=[C:9]1[C:10]2[CH:11]=[C:2]([O:1][C:22]3[CH:14]=[N:15][CH:16]=[C:17]([CH:21]=3)[C:18]([NH2:20])=[O:19])[CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 804566-ChloronicotinamideHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 66673454HCID 66673454, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Combine 7-hydroxy-1-tetralone (J. Med. Chem. (1998), 41(7), 1068-1083), (3.37 g, 20.7 mmol), 6-chloronicotinamide (available from Aldrich Chemical Company, Milwaukee, USA) (2.95 g, 18.8 mmol, K2CO3 (3.91 g, 28.3 mmol), DMA (dimethylacetamide) (45 ml) and toluene (25 ml) in a round bottom flask, equipped with Dean-Stark trap, condenser, and nitrogen inlet. Reflux the suspension for 2-3 hours before cooling to ambient temperature. Remove the solids via filtration, wash solids with EtOAc, and concentrate the filtrate/wash on a rotary evaporator. Dissolve the remaining oil in EtOAc, wash with water (2×) and brine, dry (MgSO4) and concentrate. Triturate the resulting brown solid with boiling EtOAc, cool, and collect solid via filtration to give 4.76 g of the title compound as a yellow solid. Mass Spectrum (ion spray): m/z=283 (M+1); 1HNMR (DMSO-d6): 8.56 (s, 1H), 8.25 (d, 1H), 8.02 (s, 1H), 7.52 (s, 1H), 7.48 (s, 1H), 7.42 (d, 1H), 7.35 (d, 1H), 7.12 (d, 1H), 2.95 (t, 2H), 2.60 (t, 2H), 2.05 (m, 2H).

Workup

  1. temperatureReflux the suspension for 2-3 hours
  2. customRemove the solids
  3. filtrationvia filtration
  4. washwash solids with EtOAc
  5. concentrationconcentrate the
  6. washfiltrate/wash on a rotary evaporator
  7. dissolutionDissolve the remaining oil in EtOAc
  8. washwash with water (2×) and brine
  9. dry with materialdry (MgSO4)
  10. concentrationconcentrate
  11. customTriturate the resulting brown solid with boiling EtOAc
  12. temperaturecool
  13. customcollect solid
  14. filtrationvia filtration

Sources & evidence

ORD record
ord-a84a3171ec284fb7bc677c94294084cc
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Linked notes

Loading…