Sodium Iodide → 5-(3,4-Dichlorophenyl)-3,5-dihydro-2-methyl-furo[3,2-c][1,8]naphthyridin-4(2H)-one

HRID 649559Notes

Reaction equation

HRID 649559 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[C:12](=[O:19])[C:11]3[CH2:20][CH:21]([CH3:23])[O:22][C:10]2=3)[CH:5]=[CH:6][C:7]=1[Cl:8].[I-].[Na+]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3[O:19][CH:21]([CH3:23])[CH2:20][C:11]=3[C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 139345849-(3,4-Dichlorophenyl)-3,9-dihydro-2-methyl-furo[2,3-b][1,8]naphthyridin-4(2H)-one

Product 1

HCID 139345865-(3,4-Dichlorophenyl)-3,5-dihydro-2-methyl-furo[3,2-c][1,8]naphthyridin-4(2H)-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 9-(3,4-dichlorophenyl)-3,9-dihydro-2-methyl-furo[2,3-b][1,8]naphthyridin-4(2H)-one (125 mg.) (prepared as in example 2) in dimethylacetamide (20 ml.) in an atmosphere of nitrogen was added sodium iodide (250 mg.). The solution was refluxed for 4 hrs., and it was poured over ice-water, filtered, dried and recrystallized from isopropanol to yield the desired product, m.p. 273°-274° C.

Workup

  1. temperatureThe solution was refluxed for 4 hrs
  2. filtrationfiltered
  3. customdried
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-d2a3ce9678f44147af1b88d334c37502
Source dataset
uspto-grants-1988_04
Patent number
US04740511

Reaction notes

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