Sodium Carbonate → HCID 20153985, compound

HRID 364120Notes

Reaction equation

HRID 364120 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:20][CH2:19][C:10]3[N:11]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13][C:14](=O)[C:9]=3[C:7]=2[CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:20][CH2:19][CH:10]3[N:11]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13][CH:14]=[C:9]3[C:7]=2[CH:8]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 20154005HCID 20154005, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20153985HCID 20153985, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 9.0 g of 9-methoxy-4-propyl-1,2,3,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridin-1-one in 90 ml of dry pyridine at 0° is added 0.90 g of lithium aluminium hydride. After 20 minutes at 30° the reaction is quenched with 1.8 ml of 10% sodium hydroxide, the reaction mixture is diluted with ethyl acetate, dried over magnesium sulfate and filtered. The filter cake is washed well with 10% methanol/methylene chloride and the solvent is removed in vacuo from the combined filtrates. The entire above reduction procedure is repeated on the residue using tetrahydrofuran instead of pyridine as the initial reaction solvent. The product is triturated with ether to afford a white powder which is treated with 28 ml of pyridine and 6.3 ml of phosphorus oxychloride at 65° for 30 minutes. The reaction mixture is poured onto a mixture of ice and sodium carbonate solution, and the product is extracted with ethyl acetate. After drying over magnesium sulfate, the solvent is removed in vacuo to afford, as an oil, 9-methoxy-4-propyl-2,3,4a,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridine; NMR: δ 0.90 (3H,t), 3.75 (3H,s).

Workup

  1. customAfter 20 minutes at 30° the reaction is quenched with 1.8 ml of 10% sodium hydroxide
  2. additionthe reaction mixture is diluted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. washThe filter cake is washed well with 10% methanol/methylene chloride
  6. customthe solvent is removed in vacuo from the combined filtrates
  7. customreaction solvent
  8. customThe product is triturated with ether
  9. customto afford a white powder which
  10. extractionthe product is extracted with ethyl acetate
  11. dry with materialAfter drying over magnesium sulfate
  12. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2baa6f1189ad4c6eb637fd003e7c28b5
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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