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

HRID 1739427
Notes
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Reaction equation

HRID 1739427 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])[NH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28].O>CN(C)C=O>[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]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[N:9]=2)[CH:5]=[CH:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 218408052-bromo-4-(6,7-dimethoxyphthalazin-1(2H)-on-4-yl)pyridine

Product 1

HCID 218408072-bromo-4-(6,7-dimethoxy-2-methoxycarbonylmethylphthalazin-1(2H)-on-4-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 2-bromo-4-(6,7-dimethoxyphthalazin-1(2H)-on-4-yl)pyridine (362 mg) in dimethylformamide (2 ml) is added sodium hydride (48 mg, 62.4% in oil,) with ice-cooling under nitrogen atmosphere, and the mixture is stirred at room temperature for 30 minutes. To the mixture is methyl bromoacetate (0.11 ml) under ice-cooling, and the mixture is stirred for 15 minutes. To the mixture is added water, and the mixture is extracted with ethyl acetate. The extract is washed, dried, and concentrated to give 2-bromo-4-(6,7-dimethoxy-2-methoxycarbonylmethylphthalazin-1(2H)-on-4-yl)pyridine (390 mg).

Workup

  1. temperaturecooling under nitrogen atmosphere
  2. temperaturecooling
  3. stirringthe mixture is stirred for 15 minutes
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe extract is washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2e4e22712c304cbb871830e38f156e51
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05965730

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes