2-Bromopropan-1-ol → HCID 68898772, compound

HRID 1783722Notes

Reaction equation

HRID 1783722 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([Br:16])=[N:11][NH:10][C:9]2=[O:17])=[O:5])[CH3:2].[H-].[Na+].Br[CH:21]([CH3:24])[CH2:22]O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([Br:16])=[N:11][N:10]([CH:21]([CH3:24])[CH3:22])[C:9]2=[O:17])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 117132-Bromopropan-1-olHCID 24758Sodium hydrideHCID 57856207Bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester

Product 1

HCID 68898772HCID 68898772, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

1-bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (6 g, 0.02 mol) was dissolved in DMF (60 ml). To this was added NaH (60%, 0.97 g, 0.024 mol) as a DMF suspension (5 ml). The mixture was stirred at RT for 30 min then 2-bromo-propanol (3.7 g, 0.03 mol) was added in one portion as a solution in DMF (5 ml). The reaction mixture was stirred for 48 hours whereupon LC-MS showed complete consumption of starting material. The DMF was removed under vacuum and the resulting residue was partitioned between DCM (100 ml) and water (100 ml), the organic layer was dried (MgSO4), filtered and concentrated under vacuum. The resulting yellow oil was recrystallised from MeOH to give the title compound (2.3 g, 34% yield) as a white solid. Tr=1.75 min, m/z (ES+) (M+H)+ 339 & 341

Workup

  1. stirringThe reaction mixture was stirred for 48 hours whereupon LC-MS
  2. customconsumption of starting material
  3. customThe DMF was removed under vacuum
  4. customthe resulting residue was partitioned between DCM (100 ml) and water (100 ml)
  5. dry with materialthe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe resulting yellow oil was recrystallised from MeOH

Sources & evidence

ORD record
ord-8f9f5d09829445fa868973a8c1b155cd
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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