Ammonium Hydroxide → HCID 21217726, compound

HRID 1586189Notes

Reaction equation

HRID 1586189 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) is heated on a steam bath overnight. The reaction mixture is poured onto ice waterl and then is neutralized with NH4OH. The resulting solid is collected by filtration, washed with water, dissolved in CH2Cl2, dried over MgSO4, filtered and stripped. The residue is 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. temperatureis heated on a steam bath overnight
  2. additionThe reaction mixture is poured onto ice waterl
  3. filtrationThe resulting solid is collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in CH2Cl2
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe residue is purified by column chromatography on silica gel eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1028a7fbae364cb0bc7ee851c6dd83d3
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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