Ammonium Chloride → HCID 21106569, compound

HRID 1765355Notes

Reaction equation

HRID 1765355 reaction equation
C([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:17]([CH3:19])[CH3:18])[C:9]2=[O:20])=O)C.[Li+].[BH4-].[NH4+].[Cl-]>O1CCCC1>[Br:16][C:12]1[C:13]2[C:8](=[CH:7][C:6]([CH2:4][OH:3])=[CH:15][CH:14]=2)[C:9](=[O:20])[N:10]([CH:17]([CH3:19])[CH3:18])[N:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydride2×HCID 68898772HCID 68898772, compound

Product 1

HCID 21106569HCID 21106569, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (2.3 g, 6.8 mmol) was suspended in tetrahydrofuran (THF) (50 ml) and cooled to 0° C. To the suspension was added LiBH4 (5.1 ml of a 2M solution in THF, 10.2 mmol) dropwise, the suspension was allowed to warm to room temperature and stirred for 24 hours. After this time, LC-MS showed 50% starting material remained. To this was added LiBH4 (1.7 ml of a 2M solution in THF, 3.4 mmol) and the reaction mixture was stirred for a further 3 hours. The reaction was cooled to 0° C., saturated NH4Cl (40 ml) was added and the reaction mixture was then partitioned between water (50 ml) and dichloromethane (DCM) (150 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% ethyl acetate, 20% DCM) to give the title compound (0.9 g, 43% yield) as a white solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for a further 3 hours
  3. temperatureThe reaction was cooled to 0° C.
  4. customthe reaction mixture was then partitioned between water (50 ml) and dichloromethane (DCM) (150 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% ethyl acetate, 20% DCM)

Sources & evidence

ORD record
ord-4dced36c0a204e36a4fb24cb4ce14fa9
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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