Ammonium Hydroxide → HCID 21217686, compound

HRID 375892Notes

Reaction equation

HRID 375892 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][C:15]([S:18]([CH3:21])(=[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:26]>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:26])=[C:6]2[CH:5]=[N:4]1)=[CH:14][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][CH:17]=3)[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 21217699HCID 21217699, compound

Product 1

HCID 21217686HCID 21217686, compound

Conditions

Temperature
110 °C

Procedure

A mixture of N-(1-ethylpyrazol-5-yl) -5-(methylsulfonyl) anthranilic acid of example 37 (b) and POCl3 (50 ml) was heated at 110° C. for 16 hours. The reaction mixture was poured into ice-water, neutralized with NH4OH and extracted with CH2Cl2. The CH2Cl2 layer was evaporated and the residue was purified by column chromatography on silica gel eluting with 50% ether/CH2Cl2 to afford 1.1 g of 1-ethyl-4-chloro-6-(methylsulfonyl)-1H-pyrazolo[3,4-b]quinoline, m.p. 158°-160° C.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe CH2Cl2 layer was evaporated
  3. customthe residue was purified by column chromatography on silica gel eluting with 50% ether/CH2Cl2

Sources & evidence

ORD record
ord-40a49c2f6c13445e9850370992d212d7
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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