Nitrogen → HCID 44461420, compound

HRID 2268845Notes

Reaction equation

HRID 2268845 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][NH:11][N:10]=1.N#N.[O-:24][C:25]#[N:26].[K+].[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][N:11]([C:25]([NH2:26])=[O:24])[N:10]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 9797215Phthalazine, 4-[(3,5-dichloro-4-pyridinyl)methyl]-1,2-dihydro-7-methoxy-HCID 11378442Potassium cyanate

Product 1

HCID 44461420HCID 44461420, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-1,2-dihydro-phthalazine (0.4 g, 1.24 mmoles), prepared as described in example 22, in glacial acetic acid (8 ml), under stirring and dry N2 at room temperature, was added with potassium cyanate (0.2 g, 2.48 mmoles) and the reaction mixture was left to stand for 20 hours, then poured into 10% NaOH in excess and extracted more times with CH2Cl2. The organic phases were washed with water, anhydrified and concentrated to give a residue which was flash chromatographed (eluent: hexane/ethyl acetate 3:7) to give 0.36 g of the title compound (yield: 80%). m.p.>230° C.

Workup

  1. waitthe reaction mixture was left
  2. extractionextracted more times with CH2Cl2
  3. washThe organic phases were washed with water, anhydrified
  4. concentrationconcentrated
  5. customto give a residue which
  6. customchromatographed (eluent: hexane/ethyl acetate 3:7)

Sources & evidence

ORD record
ord-2d5fe0357add43efafcf7a9be51c6a13
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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