Hydrochloric Acid → HCID 18348926, compound

HRID 2268570Notes

Reaction equation

HRID 2268570 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:19](OC)=[O:20])[CH:5]=[C:6]([CH:18]=1)[O:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)=O.C(OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:19][OH:20])[CH:5]=[C:6]([O:7][CH2:8][CH2:9][NH:11][C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)[CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 18349050HCID 18349050, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18348926HCID 18348926, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A stiired solution of 2-(5-bromo-3-methoxycarbonyl-phenoxy)-N-pyridin-4-yl-acetamide (6.61 g) in anhydrous tetrahydrofuran (200 ml) was treated with a 1M diethyl ether solution of lithium aluminium hydride (56.1 ml) over a period of 20 min. A brown precipitate appeared and the mixture was stirred at room temperature for 6 h. The reaction mixture was treated with water (2 ml) 1M sodium hydroxide solution (2 ml), water (6 ml) and then with 2M hydrochloric acid (150 ml). The reaction mixture was extracted with ethyl acetate and then basified with 2M sodium hydroxide solution. The reaction mixture was reextracted with ethyl acetate. The first organic phase was washed with saturated aqueous sodium bicarbonate and combined with the second organic phase. The combined organic phase was washed with water and dried with brine and over sodium sulphate. Concentration of the organic phase gave a gum which was found to be unsatisfactory so the gum was partitioned between ethyl acetate and 2M hydrochloric acid. The aqueous layer was separated, basified to pH 10 and extracted with ethyl acetate. The organic phase was washed with water and dried with brine and over sodium sulphate. Concentration under reduced pressure gave the title compound as an off-white solid (1.5 g).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe first organic phase was washed with saturated aqueous sodium bicarbonate
  3. washThe combined organic phase was washed with water
  4. dry with materialdried with brine and over sodium sulphate
  5. customConcentration of the organic phase gave a gum which
  6. customwas partitioned between ethyl acetate and 2M hydrochloric acid
  7. customThe aqueous layer was separated
  8. extractionextracted with ethyl acetate
  9. washThe organic phase was washed with water
  10. dry with materialdried with brine and over sodium sulphate
  11. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-bd4155dbf71f4d8cb1a422e0d6e49ae0
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

Loading…