Sulfuric Acid → HCID 66835156, compound

HRID 61902Notes

Reaction equation

HRID 61902 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:16]3[C:21]([O:22]CC4C=CC(OC)=CC=4)=[CH:20][CH:19]=[CH:18][N:17]=3)[C:9](=O)[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C:8]3[C:16]4[N:17]=[CH:18][CH:19]=[CH:20][C:21]=4[O:22][C:9]=3[C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 66834426HCID 66834426, compound

Product 1

HCID 66835156HCID 66835156, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

To the mixture of 7-methoxy-3-[3-(4-methoxy-benzyloxy)-pyridin-2-yl]-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound GT15-2, 21 mg) and ethyl acetate (0.8 ml), sulfuric acid (0.2 ml) was added. The mixture was stirred and heated at 70° C. for 5 hrs. After cooling, the reaction mixture was neutralized with 2 N aqueous solution of sodium hydroxide. The mixture was diluted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (7 mg, 50%).

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-58611dccb4184d72b2396b5ebe6a1bc4
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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