Aniline → HCID 22124678, compound

HRID 1857960Notes

Reaction equation

HRID 1857960 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][N:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([N-]C(C)C)(C)C.[Li+]>C1COCC1.C(O)(=O)C>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][N:3]=[C:2]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 6115AnilineHCID 2724682Lithium diisopropylamideHCID 22124621HCID 22124621, compound

Product 1

HCID 22124678HCID 22124678, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (XV, where R2 is ethyl) (100 mg, 0.52 mmol) and aniline (120 mg, 1.3 mmol) in THF (5.0 mL) under nitrogen at -78° C. was treated with a solution (1.2 mL, 1.8 mmol) of lithium diisopropylamide (1.5 M in cyclohexane), then the temperature was allowed to rise slowly to 20° C. overnight. The resulting solution was treated with 3 drops of glacial acetic acid and concentrated to a brown residue that was purified by silica gel chromatography eluting with EtOAc. The product fractions were pooled and concentrated to a solid that was crystallized to give 1-ethyl-7-phenylamino-1H -[1,6]naphthyridin-2-one (33 mg, 24%): mp (8:1 hexanes/dichloromethane) 174-175° C.

Workup

  1. concentrationconcentrated to a brown residue that
  2. customwas purified by silica gel chromatography
  3. washeluting with EtOAc
  4. concentrationconcentrated to a solid
  5. customthat was crystallized

Sources & evidence

ORD record
ord-ade1708230494260afbf811e0e41eb7e
Source dataset
uspto-grants-2000_11
Patent number
US06150359

Reaction notes

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