Aluminium lithium hydride → 2-anilino-6-fluoro-7-(hydroxymethyl)-1-phenyl-1,8-naphthyridin-4(1H)-one

HRID 1839399Notes

Reaction equation

HRID 1839399 reaction equation
[NH:1]([C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[N:15]=[C:14]([C:24](OCC)=[O:25])[C:13]([F:29])=[CH:12][C:11]=2[C:10](=[O:30])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:1]([C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[C:11]([C:10](=[O:30])[CH:9]=1)=[CH:12][C:13]([F:29])=[C:14]([CH2:24][OH:25])[N:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21948195Ethyl 7-anilino-3-fluoro-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxylate

Product 1

HCID 219481342-anilino-6-fluoro-7-(hydroxymethyl)-1-phenyl-1,8-naphthyridin-4(1H)-oneYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. suspension of ethyl 7-anilino-3-fluoro-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxylate (100.0 mg, 0.25 mmol) in THF (2.5 mL) was added LAH (0.750 mmol, 1M in THF) dropwise over 10 min. After 5 min. the reaction was slowly quenched with EtOAc (10 mL), was left to stir for 15 min and was concentrated in vacuo. The resiude was taken up in CH2Cl2 (10 mL) and 1N HCl (5 mL) and was left to stir for 30 min. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo. Trituation with Et2O provided 2-anilino-6-fluoro-7-(hydroxymethyl)-1-phenyl-1,8-naphthyridin-4(1H)-one (55.2 mg, 61%) as a tan solid: LCMS RT: 2.01 min, MH+: 362.3.

Workup

  1. customAfter 5 min. the reaction was slowly quenched with EtOAc (10 mL)
  2. waitwas left
  3. concentrationwas concentrated in vacuo
  4. wait1N HCl (5 mL) and was left
  5. stirringto stir for 30 min
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5212dd79f7d04e43a030b349f348bf23
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

Loading…