Sodium Hydroxide → HCID 11824456, compound

HRID 863764Notes

Reaction equation

HRID 863764 reaction equation
C([C:3]1([C:15]2[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[N:16]=2)[C:12]2[C:7](=[C:8]([Cl:14])[CH:9]=[CH:10][C:11]=2[Cl:13])[C:5](=[O:6])[O:4]1)#N.[OH-:25].[Na+]>CO.O>[Cl:13][C:11]1[CH:10]=[CH:9][C:8]([Cl:14])=[C:7]2[C:12]=1[C:3]([C:15]1[N:16]=[C:17]([O:23][CH3:24])[CH:18]=[C:19]([O:21][CH3:22])[N:20]=1)([OH:25])[O:4][C:5]2=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19050644HCID 19050644, compound

Product 1

HCID 11824456HCID 11824456, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

70 g of 3-cyano-4,7-dichloro-3-(4,6-dimethoxy-2-pyrimidinyl)phthalide are slurried in 100 ml of methanol and 16 g of NaOH pellets with 125 ml of water added. The mixture is stirred and heated to reflux for 30 mins., the solution cooled and the methanol stripped. The aqueous solution was diluted with 400 ml of water, washed with 100 ml of ether and then added dropwise to 400 ml of 1 NH2SO4 to give a solid which is filtered and dried in vacuum for 1 hr at 60°. The solid is triturated with 100 ml of ether and the suspension left overnight at RT and the solid isolated by filtration to give the title product m.p. 161°-175° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 mins
  3. temperature, the solution cooled
  4. washwashed with 100 ml of ether
  5. additionadded dropwise to 400 ml of 1 NH2SO4
  6. customto give a solid which
  7. filtrationis filtered
  8. customdried in vacuum for 1 hr at 60°
  9. customThe solid is triturated with 100 ml of ether
  10. customthe solid isolated by filtration

Sources & evidence

ORD record
ord-97b5b7b95ce848f689af10065902c8e1
Source dataset
uspto-grants-1996_10
Patent number
US05561101

Reaction notes

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