Benzyl Bromide → 1,4-Dihydro-1-phenylmethylbenzo[c]-1,5-naphthyridin-2(3H)-one

HRID 652245Notes

Reaction equation

HRID 652245 reaction equation
[NH:1]1[C:10](=[O:11])[CH2:9][CH2:8][C:7]2[N:6]=[CH:5][C:4]3[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=3[C:2]1=2.[OH-].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CS(C)=O.O>[C:19]1([CH2:18][N:1]2[C:10](=[O:11])[CH2:9][CH2:8][C:7]3[N:6]=[CH:5][C:4]4[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=4[C:2]2=3)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 136625093,4-Dihydrobenzo[c][1,5]naphthyridin-2(1H)-one

Product 1

HCID 138852451,4-Dihydro-1-phenylmethylbenzo[c]-1,5-naphthyridin-2(3H)-oneYield 84.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A stirred solution of 1,4-dihydrobenzo[c]-1,5-naphthyridin-2(3H)-one (3.97 g) in dimethylsulfoxide (sieve dried, 80 ml) was treated sequentially with powdered potassium hydroxide (2.64 g of 85% KOH) and benzyl bromide (3.76 g). The solution was stirred for 1.5 hours at ambient temperature, transferred to a separatory funnel, diluted with water (400 ml) and extracted with ethyl acetate (2×250 ml). The organic phase was washed with water (2×200 ml), dried (Na2SO4), filtered and evaporated to give a solid (4.9 g). Recrystallization from 95% ethanol (32 ml) gave 3.35 g of crystals, m.p. 153.5°-155.5° C.

Workup

  1. customtransferred to a separatory funnel
  2. extractionextracted with ethyl acetate (2×250 ml)
  3. washThe organic phase was washed with water (2×200 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-88856f47a24149ad82c4b4864b734c86
Source dataset
uspto-grants-1987_06
Patent number
US04670562

Reaction notes

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