Ammonium Hydroxide → HCID 21217727, compound

HRID 1586140Notes

Reaction equation

HRID 1586140 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].[NH4+].[OH-].O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:11]1[C:10]2[C:9](=[C:17]([O:18][CH3:19])[CH:16]=[CH:15][CH:14]=2)[N:8]=[C:7]2[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=12

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 21217694HCID 21217694, compound

Product 1

HCID 21217727HCID 21217727, compound

Procedure

A mixture of N-(1-ethylpyrazol-5-yl)-3-methoxyanthranilic acid of example 9(d) and POCl3 (50 ml) is refluxed overnight. The reaction mixture is poured into ice waterl, neutralized with NH4OH and the mixture is extracted with CH2Cl2 (3×150 ml). The CH2Cl2 extracts are combined, dried over MgSO4, filtered and evaporated. The residue is purified by column chromatography on silica gel eluting with 35% EtOAc/hexane to afford 0.4 g of 4-chloro-1-ethyl-8-methoxy-1H-pyrazolo[3,4-b]quinoline, m.p. 168°-170° C.

Workup

  1. temperatureis refluxed overnight
  2. additionThe reaction mixture is poured into ice waterl
  3. extractionthe mixture is extracted with CH2Cl2 (3×150 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column chromatography on silica gel eluting with 35% EtOAc/hexane

Sources & evidence

ORD record
ord-dc26b476ad434932aa5393b2dac25b5a
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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