P-Anisidine → HCID 22124701, compound

HRID 1857961Notes

Reaction equation

HRID 1857961 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.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=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:23][C:20]3[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=3)[CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 2724682Lithium diisopropylamideHCID 22124621HCID 22124621, compound

Product 1

HCID 22124701HCID 22124701, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (XV, where R2 is ethyl) (100 mg, 0.52 mmol) and p-anisidine (160 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 1:1 EtOAc hexanes then EtOAc. The product fractions were pooled and concentrated to a solid that was crystallized to give 1-ethyl-7-(4-methoxyphenylamino)-1H -[1,6]naphthyridin-2-one (87 mg, 57%): mp (2-propanol) 165-166° C.

Workup

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

Sources & evidence

ORD record
ord-a065729316d74022bb1a2b1b6a0fcf5c
Source dataset
uspto-grants-2000_11
Patent number
US06150359

Reaction notes

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