Ammonium Hydroxide → HCID 21217686, compound

HRID 1586176Notes

Reaction equation

HRID 1586176 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) is heated at 110° C. for 16 hours. The reaction mixture is poured into ice water, neutralized with NH4OH and extracted with CH2Cl2. The CH2Cl2 layer is evaporated, and the residue is purified by column chromatography on silica gel eluting with 50% ether/H2Cl2 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 is evaporated
  3. customthe residue is purified by column chromatography on silica gel eluting with 50% ether/H2Cl2

Sources & evidence

ORD record
ord-234890ea21a34dfb8fecf699c43a0660
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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