Hydrochloric Acid → 6-tert-butyl-2-[3-chloro-2-(hydroxymethyl)phenyl]-8-(hydroxymethyl)phthalazin-1(2H)-one

HRID 1025559Notes

Reaction equation

HRID 1025559 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:25]=[O:26])[C:8]2[C:9](=[O:24])[N:10]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=3[CH2:22][OH:23])[N:11]=[CH:12][C:13]=2[CH:14]=1)([CH3:4])([CH3:3])[CH3:2].ClC(Cl)C.[BH4-].[Na+].Cl>CO>[C:1]([C:5]1[CH:14]=[C:13]2[C:8](=[C:7]([CH2:25][OH:26])[CH:6]=1)[C:9](=[O:24])[N:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=1[CH2:22][OH:23])[N:11]=[CH:12]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 4311764Sodium borohydrideHCID 866737047-Tert-butyl-3-[3-chloro-2-(hydroxymethyl)phenyl]-4-oxo-3,4-dihydrophthalazine-5-carbaldehyde

Product 1

HCID 710084996-tert-butyl-2-[3-chloro-2-(hydroxymethyl)phenyl]-8-(hydroxymethyl)phthalazin-1(2H)-oneYield 26.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above 7-tert-butyl-3-[3-chloro-2-(hydroxymethyl)phenyl]-4-oxo-3,4-dihydrophthalazine-5-carbaldehyde (147 mg, 0.396 mmol) was combined with dichloroethane (5 mL) and methanol (5 mL) to give a yellow solution. Sodium borohydride (27 mg, 0.714 mmol) was added and the mixture was stirred at room temperature for 4 hrs. The mixture was treated with 1N hydrochloric acid and extracted with dichloromethane. The organic layer was washed with brined and dried over sodium sulfate. After the evaporation of solvents, the residue was purified by flash column chromatography (silica gel 40 g, 0% to 40% ethyl acetate in heptane) to give 6-tert-butyl-2-[3-chloro-2-(hydroxymethyl)phenyl]-8-(hydroxymethyl)phthalazin-1(2H)-one as a light yellow solid (39 mg, 26.4%). LC/MS calcd for C20H21ClN2O3 (m/e) 372.12, obsd 371.1 (M−H, ES−).

Workup

  1. customto give a yellow solution
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brined and
  4. dry with materialdried over sodium sulfate
  5. customAfter the evaporation of solvents
  6. customthe residue was purified by flash column chromatography (silica gel 40 g, 0% to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-072e5456f2514ac6a2ac18206dfb292e
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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