Ammonium Hydroxide → HCID 67157027, compound

HRID 549262Notes

Reaction equation

HRID 549262 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N+:16]([O-])=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+].O=P(Cl)(Cl)[Cl:25]>>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3[Cl:25])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 67158211HCID 67158211, compound

Product 1

HCID 67157027HCID 67157027, compoundYield 27%

Procedure

A solution of 6-benzenesulfonyl-quinoline 1-oxid (135 mg, 0.47 mmol) in POCl3 (4 mL) was heated at 90° C. for 2 h after which the solution was poured on ice, ammonium hydroxide was added and extraction with DCM. The organic phase was dried (NaSO4), the volatiles were evaporated and the residue was purified by column chromatography (SiO2, ethyl acetate:petroleum ether, 1:1) to yield a white solid (39 mg, 27%). MS m/z: 305 [M+H+].

Workup

  1. additionwas added
  2. extractionextraction with DCM
  3. dry with materialThe organic phase was dried (NaSO4)
  4. customthe volatiles were evaporated
  5. customthe residue was purified by column chromatography (SiO2, ethyl acetate:petroleum ether, 1:1)

Sources & evidence

ORD record
ord-b1ddf23411fe4dcc81a7d5266f021f71
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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