Sodium hydride → HCID 22397281, compound

HRID 1070537Notes

Reaction equation

HRID 1070537 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([Cl:24])=[N:16][N:15]=1>C1COCC1.[NH4+].[Cl-]>[Cl:24][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([CH:8]([C:5]2[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=2)[C:9]#[N:10])=[N:15][N:16]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 784901,4-DichlorophthalazineHCID 123966084-Pyridylacetonitrile hydrochloride

Product 1

HCID 22397281HCID 22397281, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

4-Pyridylacetonitrile hydrochloride (5.00 g, 32.3 mmol) in 40 mL of THF was sonicated for 10 min, and the mixture was added to 10 mL THF solution of NaH (1.55 g, 64.7 mmol) using dripping funnel while the temperature was kept below 15° C. After the addition, the mixture was cooled to 0° C. and 1,4-dichlorophthalazine (3.22 g, 24.3 mmol) was added to the mixture. The mixture turned into red instantly. The reaction was continued for another 4 hrs, and the mixture was poured in cold NH4Cl solution. The resulting red solid was filtered, washed with H2O, and dried to give 4.4 g of 1-chloro-4-(4-pyridylcyanomethyl)phthalazine (65%); mp 265° C. (dec); 1H NMR (CDCl3) δ 6.00 (s, 1H), 7.39-8.60 (m, 8H); LC/MS MH+281.4.

Workup

  1. customwas kept below 15° C
  2. additionAfter the addition
  3. filtrationThe resulting red solid was filtered
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-908e9e896204466798f07002233e9cf3
Source dataset
uspto-grants-2005_06
Patent number
US06903101B1

Reaction notes

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