Aluminium lithium hydride → 7-(4-methoxybenzyl)-4-hydroxy-3-(hydroxymethyl)-1,7-naphthyridin-8(7H)-one

HRID 1668977Notes

Reaction equation

HRID 1668977 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[C:17](=[O:18])[C:16]3[N:15]=[CH:14][C:13]([C:19](OCC)=[O:20])=[C:12]([OH:24])[C:11]=3[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:17](=[O:18])[C:16]3[N:15]=[CH:14][C:13]([CH2:19][OH:20])=[C:12]([OH:24])[C:11]=3[CH:10]=[CH:9]2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178469681HCID 178469681, compound

Product 1

HCID 1784907707-(4-methoxybenzyl)-4-hydroxy-3-(hydroxymethyl)-1,7-naphthyridin-8(7H)-oneYield 37.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

Ethyl 7-(4-methoxybenzyl)-4-hydroxy-8-oxo-7,8-dihydro-1,7-naphthyridine-3-carboxylate (4.00 g, 11 mmol) was suspended in anhydrous THF (60 ml) and the mixture was cooled down to −10° C. Lithium aluminum hydride 2M in THF (11 ml, 23 mmol) was added dropwise to the mixture. The cold bath was then removed and the reaction was stirred for two hours at room temperature. Sodium sulfate decahydrate (10 g) was added portionwise to the reaction. The mixture was stirred for 3 hours and then filtered. The cake collected in the filter funnel was extracted for 12 hours in a soxhlet apparatus in a 2:1 mixture of chloroform and methanol. The filtrate was directly loaded unto silica gel and purified by column chromatography on silica gel using a gradient of 0 to 10% methanol in DCM to give 7-(4-methoxybenzyl)-4-hydroxy-3-(hydroxymethyl)-1,7-naphthyridin-8(7H)-one (1.3 g, 37% yield) as light yellow solid. MS (M+H)+ 313.

Workup

  1. customThe cold bath was then removed
  2. additionSodium sulfate decahydrate (10 g) was added portionwise to the reaction
  3. stirringThe mixture was stirred for 3 hours
  4. filtrationfiltered
  5. customThe cake collected in the filter funnel
  6. extractionwas extracted for 12 hours in a soxhlet apparatus in a 2:1 mixture of chloroform and methanol
  7. custompurified by column chromatography on silica gel using a gradient of 0 to 10% methanol in DCM

Sources & evidence

ORD record
ord-344a031b027843c6a15180cf00ac7547
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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