Sodium hydride → HCID 18381603, compound

HRID 2297477Notes

Reaction equation

HRID 2297477 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[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)[C:12]([C:21]#[C:22]C(C)(O)C)=[N:11][N:10]=1.[H-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[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)[C:12]([C:21]#[CH:22])=[N:11][N:10]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18381655HCID 18381655, compound

Product 1

HCID 18381603HCID 18381603, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a Claisen flask, a suspension under N2 of 4-[4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-phthalazin-1-yl]-2-methyl-but-3-yn-2-ol (0.4 g, 1 mmole), prepared as described in example 107, in dry toluene (50 ml) was added with a catalytic amount of NaH, the mixture was refluxed, then distilled up to half volume. The mixture was left to stand overnight, then poured into water, extracted three times with CH2Cl2, discoloured with charcoal, filtered over celite and dried to give a solid which was triturated in ethyl ether to give 0.21 g of the title compound. m.p.: 210.3-211.3° C. (dec.).

Workup

  1. temperaturethe mixture was refluxed
  2. distillationdistilled up to half volume
  3. waitThe mixture was left
  4. additionpoured into water
  5. extractionextracted three times with CH2Cl2
  6. filtrationfiltered over celite
  7. customdried
  8. customto give a solid which
  9. customwas triturated in ethyl ether

Sources & evidence

ORD record
ord-6e0996b390704733a9dbf7470f6604a3
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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