Potassium Carbonate → HCID 59401310, compound

HRID 2060895Notes

Reaction equation

HRID 2060895 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.Cl[C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][N:16]=1.C([O-])([O-])=[O:24].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O:1][C:15]2[CH:20]=[C:19]([CH:18]=[CH:17][N:16]=2)[C:21]([NH2:22])=[O:24])=[CH:3][CH:4]=1)=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3442904-Hydroxy-1-naphthaldehydeHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 59401310HCID 59401310, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-hydroxy-1-naphthaldehyde (500 mg, 2.9 mmol) and 2-chloro-4-cyanopyridine (402 mg, 2.9 mmol) in DMF (4 mL) was added K2CO3 (2.01 g, 14.52 mmol). The reaction was heated for 1 h at 70° C. in a microwave. The mixture was diluted with EtOAc (100 mL), washed with water (2×50 mL) and the aqueous phase extracted with EtOAc (2×50 mL). The organic phase was washed with water (100 mL), 1M NaOH (3×60 mL), brine (50 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (SiO2, NH4OH:MeOH:DCM, 0.2:2:98) to give the title compound: RT=3.02 min; m/z (ES+)=293.1 [M+H]+.

Workup

  1. washwashed with water (2×50 mL)
  2. extractionthe aqueous phase extracted with EtOAc (2×50 mL)
  3. washThe organic phase was washed with water (100 mL), 1M NaOH (3×60 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo
  6. customthe residue purified by column chromatography (SiO2, NH4OH:MeOH:DCM, 0.2:2:98)

Sources & evidence

ORD record
ord-39107b57fd5b4326ab6fd1c07cd421e0
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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