Ammonium Hydroxide → HCID 10666432, compound

HRID 1872047Notes

Reaction equation

HRID 1872047 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:19]2[C:14](=[C:15]([CH3:21])[CH:16]=[C:17]([Cl:20])[N:18]=2)[C:13](C#N)=[CH:12]1.[OH-].[NH4+]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:19]2[C:14](=[C:15]([CH3:21])[CH:16]=[C:17]([Cl:20])[N:18]=2)[CH:13]=[CH:12]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10739049HCID 10739049, compound

Product 1

HCID 10666432HCID 10666432, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 52 mg of 1-(2-bromo-4-isopropylphenyl)-6-chloro-3-cyano-4-methyl-7-azaindole and 10 mL of 65% sulfuric acid was refluxed for one hour. The cooled solution was poured onto ice, and 17 mL of conc. ammonium hydroxide was added. The alkaline mixture was extracted with ethyl acetate. The extract was washed (brine), dried (Na2SO4), and evaporated. TLC of the residue on silica gel with 70:30 hexane-ethyl acetate showed a major new spot, Rf =0.58, with a trace of unchanged starting material (Rf 0.52). The crude product was purified by preparative TLC to give 39 mg of non-crystalline product, which slowly crystallized on standing. Mass spec. (m+H)+ =363.0247; calcd., 363.0264 (79Br, 35Cl).

Workup

  1. temperaturewas refluxed for one hour
  2. additionwas added
  3. extractionThe alkaline mixture was extracted with ethyl acetate
  4. washThe extract was washed (brine)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-e36ffa28fb2d4f198b937712b8bf3bd6
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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