Ammonium Hydroxide → HCID 21217727, compound

HRID 375856Notes

Reaction equation

HRID 375856 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) was refluxed overnight. The reaction mixture was poured into ice-water, neutralized with NH4OH and the mixture was extracted with CH2Cl2 (3×150 ml). The CH2Cl2 extracts were combined, dried over MgSO4, filtered and evaporated. The residue was 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. temperaturewas refluxed overnight
  2. extractionthe mixture was extracted with CH2Cl2 (3×150 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with 35% EtOAc/hexane

Sources & evidence

ORD record
ord-50d4c43a6bb2421297fb847a462a79d5
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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