Water → HCID 18999839, compound

HRID 2260119Notes

Reaction equation

HRID 2260119 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:11]2=[CH:12][C:13]3[N:14]=[C:15]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([F:28])[CH:21]=4)[CH:16]=[N:17][C:18]=3[CH:19]=[C:10]2[CH:9]=[N:8]1)(=O)C.[Li+].[OH-].O>C1COCC1.CO.O>[OH:4][CH2:5][CH2:6][N:7]1[C:11]2=[CH:12][C:13]3[N:14]=[C:15]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([F:28])[CH:21]=4)[CH:16]=[N:17][C:18]=3[CH:19]=[C:10]2[CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 18999834HCID 18999834, compound

Product 1

HCID 18999839HCID 18999839, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a mixture of 0.36 g of 1-(2-acetoxyethyl)-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline in 50 ml of THF:MeOH:H2O (3:1:1) is added 0.39 g of LiOH:H2O and the resulting mixture is stirred at room temperature overnight. The MeOH and THF are removed in vacuo and the yellow crystalline solid precipitates out from the aqueous solution. More water is added to the mixture and cooled in an ice-bath for 1/2 hour. The product is collected by filtration, washed with water and air dried. The product is recrystallized from ethylacetate, collected and air dried to obtain 1-[2-hydroxyethyl]-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline (m.p. 192°-195° C.).

Workup

  1. customThe MeOH and THF are removed in vacuo
  2. customthe yellow crystalline solid precipitates out from the aqueous solution
  3. additionMore water is added to the mixture
  4. temperaturecooled in an ice-bath for 1/2 hour
  5. filtrationThe product is collected by filtration
  6. washwashed with water and air
  7. customdried
  8. customThe product is recrystallized from ethylacetate
  9. customcollected
  10. customair dried

Sources & evidence

ORD record
ord-14f2a0c8dbdf416db677d83f6d6e4649
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Reaction notes

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