Methanol → 2-bromo-4-(6,7-dimethoxy-2-hydroxyethylphthalazin-1(2H)-on-4-yl)pyridine

HRID 1739428Notes

Reaction equation

HRID 1739428 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[C:11](=[O:22])[N:10]([CH2:23][C:24](OC)=[O:25])[N:9]=2)[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+].CO.O>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[C:11](=[O:22])[N:10]([CH2:23][CH2:24][OH:25])[N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 218408072-bromo-4-(6,7-dimethoxy-2-methoxycarbonylmethylphthalazin-1(2H)-on-4-yl)pyridine

Product 1

HCID 218408512-bromo-4-(6,7-dimethoxy-2-hydroxyethylphthalazin-1(2H)-on-4-yl)pyridineYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromo-4-(6,7-dimethoxy-2-methoxycarbonylmethylphthalazin-1(2H)-on-4-yl)pyridine (4.34 g) in tetrahydrofuran (20 ml) is added sodium borohydride (0.76 g), and further thereto is added dropwise with heating a mixture of methanol (3.2 ml) and tetrahydrofuran (5 ml) under reflux over a period of one hour. The reaction mixture is allowed to stand for cooling, and thereto is added water under ice-cooling. The mixture is extracted with chloroform, and the extract is washed, dried and concentrated. The residue is recrystallized from isopropyl ether to give 2-bromo-4-(6,7-dimethoxy-2-hydroxyethylphthalazin-1(2H)-on-4-yl)pyridine (3.08 g).

Workup

  1. additionfurther thereto is added dropwise
  2. temperaturewith heating
  3. temperatureunder reflux over a period of one hour
  4. temperaturefor cooling
  5. temperaturecooling
  6. extractionThe mixture is extracted with chloroform
  7. washthe extract is washed
  8. customdried
  9. concentrationconcentrated
  10. customThe residue is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-1864bd7b8e23474ea8bd76353817e282
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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