HCID 18348915, compound → HCID 18349112, compound

HRID 2268565Notes

Reaction equation

HRID 2268565 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[O:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:20][C:18]1[CH:19]=[C:3]([CH2:1][OH:2])[CH:4]=[C:5]([O:6][CH2:7][CH2:8][NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 18348915HCID 18348915, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18349112HCID 18349112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
1 °C

Procedure

A suspension of 2-(3-formyl-5-methyl-phenoxy)-N-pyridin-4-yl-acetamide (0.30 g) in anhydrous tetahydrofuran (1 ml), stirring under a nitrogen atmosphere, was cooled to about 1° C. and treated with a 1M tetrahydrofuran solution of lithium aluminium hydnde (5.47 ml) over a period of 3 min. After 15 min the mixture was allowed to warm to room temperature. After stirring for a further 22 h the mixture was cooled to about 2° C. and the excess reagent was quenched with cautious dropwise addition of wet tetrahydrofuran and then water. The resulting aqueous mixture was partitioned between ethyl acetate and dilute sodium hydroxide solution saturated with sodium chloride and ammonium sulphate. The organic phase was dried with magnesium sulphate and concentrated under reduced pressure and the resulting gum was triturated with diethyl ether giving, after drying, the title compound as an off-white solid (0.13 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringAfter stirring for a further 22 h the mixture
  3. temperaturewas cooled to about 2° C.
  4. customthe excess reagent was quenched with cautious dropwise addition of wet tetrahydrofuran
  5. customThe resulting aqueous mixture was partitioned between ethyl acetate and dilute sodium hydroxide solution saturated with sodium chloride and ammonium sulphate
  6. dry with materialThe organic phase was dried with magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting gum was triturated with diethyl ether giving
  9. customafter drying

Sources & evidence

ORD record
ord-7ba82976cd984ca6ac34db20caab911f
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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