Ammonium Hydroxide → HCID 21217726, compound

HRID 375905Notes

Reaction equation

HRID 375905 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][C:15]([S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])=[CH:16][CH:17]=2)[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].[NH4+].[OH-].O=P(Cl)(Cl)[Cl:29]>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:29])=[C:6]2[CH:5]=[N:4]1)=[CH:14][C:15]([S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])=[CH:16][CH:17]=3)[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 21217701HCID 21217701, compound

Product 1

HCID 21217726HCID 21217726, compound

Procedure

A mixture of N-(1-ethylpyrazol-5-yl) -5-(trifluoromethylsulfonyl)anthranilic acid and POCl3 (30 mL) was heated on a steam bath overnight. The reaction mixture was poured onto ice-water and then was neutralized with NH4OH. The resulting solid was collected by filtration, washed with water, dissolved in CH2Cl2, dried over MgSO4, filtered and stripped. The residue was purified by column chromatography on silica gel eluting with 10% ethyl acetate/hexane to afford 1.0 g of 1-ethyl-4-chloro-6-(trifluoromethylsulfonyl)-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperaturewas heated on a steam bath overnight
  2. additionThe reaction mixture was poured onto ice-water
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in CH2Cl2
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe residue was purified by column chromatography on silica gel eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-573899cc711c4c5196ee2452ed0c7212
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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