Phthalazine → HCID 21814495, compound

HRID 1952773Notes

Reaction equation

HRID 1952773 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][N:2]=1.[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+]>O1CCCC1>[C:11]1([CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[N:3][NH:2]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 9207PhthalazineHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 21814495HCID 21814495, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4 g of phthalazine in 50 ml of tetrahydrofuran is added dropwise at room temperature to a solution of phenyl-magnesium bromide (prepared from 6 g of bromobenzene and 1 g of magnesium in 30 ml of tetrahydrofuran). The reaction mixture is held at reflux for 6 hrs. After cooling the mixture is treated with a saturated aqueous solution of ammonium chloride and extracted 3 times with diethyl ether. The organic phases are combined, dried and subsequently triturated with pentane. 2.32 g of not quite pure 1-phenyl-1,2-dihydro-phthalazine are isolated as a yellowish solid, m.p. 79° C.

Workup

  1. temperatureat reflux for 6 hrs
  2. temperatureAfter cooling the mixture
  3. extractionextracted 3 times with diethyl ether
  4. customdried
  5. customsubsequently triturated with pentane

Sources & evidence

ORD record
ord-f347a3885e3a44f0b5559b46af346e0f
Source dataset
uspto-grants-2000_09
Patent number
US06114330

Reaction notes

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