Furfural → 4-Furan-2-ylmethyl-7-methoxy-2H-phthalazin-1-one

HRID 2297492Notes

Reaction equation

HRID 2297492 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH:9]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)O[C:7]2=[O:32].[CH:33](=O)[C:34]1[O:38][CH:37]=[CH:36][CH:35]=1.C(N(CC)CC)C.O.[NH2:48][NH2:49]>C(Cl)Cl>[O:38]1[CH:37]=[CH:36][CH:35]=[C:34]1[CH2:33][C:9]1[C:10]2[C:6](=[CH:5][C:4]([O:3][CH3:2])=[CH:12][CH:11]=2)[C:7](=[O:32])[NH:49][N:48]=1

Participants

6

Reactant 4

HCID 7362FurfuralHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 11562468(5-Methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)triphenyl phosphonium bromide

Product 1

HCID 183816674-Furan-2-ylmethyl-7-methoxy-2H-phthalazin-1-oneYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (5-methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-triphenyl-phosphonium bromide (8 g, 15.83 mmoles), prepared as described in example 36, CH2Cl2 (100 ml) and furfural (1.31 ml, 15.83 mmoles), cooled in ice and under N2, was dropwise added with triethylamine (2.2 ml, 15.83 mmoles). The cooling was removed and the mixture was stirred for 1.5 hours, then washed with water, anhydrified over Na2SO4 and dried. The residue was dissolved in CH3OH (50 ml) and added with hydrazine monohydrate (2.3 ml, 47.49 mmoles). The mixture was refluxed for 1 hour, then concentrated to half volume. A precipitate crystallised and dried under vacuum at 40° C. gave 1.82 g of the title compound (yield: 45%).

Workup

  1. customprepared
  2. temperaturecooled in ice and under N2
  3. customThe cooling was removed
  4. washwashed with water
  5. customdried
  6. dissolutionThe residue was dissolved in CH3OH (50 ml)
  7. temperatureThe mixture was refluxed for 1 hour
  8. concentrationconcentrated to half volume
  9. customA precipitate crystallised
  10. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-11e8e72f9668482486da914ec0d83de6
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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