Water → HCID 13771602, compound

HRID 867395Notes

Reaction equation

HRID 867395 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[C:4](=[O:20])[C:3]=1[CH2:21][CH2:22][CH2:23][CH2:24][OH:25].BrBr.N12CCCN=C1CCCCC2.O>C(Cl)Cl>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][N:7]=3)[C:2](=[O:1])[C:3]3([CH2:21][CH2:22][CH2:23][CH2:24][O:25]3)[C:4]2=[O:20])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54738147HCID 54738147, compound

Product 1

HCID 13771602HCID 13771602, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 4-Hydroxy--(4-hydroxybutyl)-1-(3-methoxyphenyl)(1,8)-naphthyridin-2(1H)-one (1 g.)in methylene chloride (10 ml),in an ice-acetone bath was added a solution of bromine (0.5 g.) in methylene chloride (5 ml.) over a period of 15 min. The resulting yellow-orange suspension was stirred overnight at room temperature. To the resulting clear yellow solution was added a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (1 g.), in methylene chloride (5 ml.) during 5 mins. The mixture was stirred at room temperature for 3 hrs. after which time water (5 ml) was added. The organic layer was separated, dried and evaporated. To the residue was added 50% aqueous ethanol (10 ml.) and after some time the solid was filtered off and recrystallized from isopropanol to yield 1-(3-methoxyphenyl)-3', 4',5', 6'-tetrahydrospiro[1,8-naphthyridine-3,2'-(2 H)pyran]-2, 4-dione, m.p. 181°-183° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hrs
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated
  5. additionTo the residue was added 50% aqueous ethanol (10 ml.)
  6. filtrationafter some time the solid was filtered off
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-b7e334e56cb14497965307256307bee0
Source dataset
uspto-grants-1988_10
Patent number
US04775524

Reaction notes

Loading…