Nitrogen → HCID 44461430, compound

HRID 2268884Notes

Reaction equation

HRID 2268884 reaction equation
N#N.[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:23])[C:9]=1[CH2:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH2:14][NH:13][N:12]=1.[C:24]([N:31]1C=CN=C1)(N1C=CN=C1)=[O:25].Cl.N[OH:38]>C1COCC1.C(O)C.CCCCCC.C(OCC)(=O)C.C(Cl)Cl.CO>[OH:38][NH:31][C:24]([N:13]1[N:12]=[C:11]([CH2:10][C:9]2[C:8]([Cl:23])=[CH:7][N:6]=[CH:5][C:4]=2[Cl:3])[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH2:14]1)=[O:25]

Participants

9

Reactant 4

HCID 947NitrogenHCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 9797215Phthalazine, 4-[(3,5-dichloro-4-pyridinyl)methyl]-1,2-dihydro-7-methoxy-

Product 1

HCID 44461430HCID 44461430, compoundYield 25.4%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

At room temperature, under stirring and N2, a solution of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-1H-phthalazine (1 g, 3.1 mmoles), prepared as described in example 22, in THF (35 ml), was added with 1,1′-carbonyldiimidazole (0.55 g, 3.41 mmoles) and refluxed, then concentrated and taken up in ethanol. Hydroxylamine hydrochloride (0.26 g, 3.72 mmoles) in ethanol was added. After 10 hours under reflux, the mixture was cooled, concentrated and partitioned between water and CH2Cl2. The organic phase was washed with water, anhydrified and brought to dryness to give a residue which was flash chromatographed (eluent: CH2Cl2/CH3OH 98:2, then hexane/ethyl acetate 3:7) to give 0.3 g of the title compound (yield: 25%). m.p.: 155-158° C.

Workup

  1. temperaturerefluxed
  2. concentrationconcentrated
  3. temperatureAfter 10 hours under reflux
  4. temperaturethe mixture was cooled
  5. concentrationconcentrated
  6. custompartitioned between water and CH2Cl2
  7. washThe organic phase was washed with water
  8. customto give a residue which
  9. customchromatographed (eluent

Sources & evidence

ORD record
ord-2e39d3d98b0b4e22b5fcef7e2809b284
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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