Ammonium Hydroxide → HCID 10497535, compound

HRID 1251488Notes

Reaction equation

HRID 1251488 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]([CH3:20])[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]([CH3:20])[N:18]=2)[CH:13]=[CH:12]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10737736HCID 10737736, compound

Product 1

HCID 10497535HCID 10497535, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 4.00 g of 1-(2-bromo-4-isopropylphenyl)-3-cyano-4,6-dimethyl-7-azaindole and 40 mL of 65% sulfuric acid was refluxed for one hour. The solution was cooled and poured onto ice. Conc. ammonium hydroxide was added until the mixture was alkaline to pH paper. The mixture was extracted with ethyl acetate. The solution was dissolved in 60:40 hexane-ethyl acetate and passed through a short column of silica gel. The eluate was evaporated, and the residue was crystallized from 20 mL of hexane to give 2.45 g (66% yield) of 1-(2-bromo-4-isopropylphenyl)-4,6-dimethyl-7-azaindole. Mass spec: (m+H)+=343.0818; calculated, 343.0810. Rf=0.57 on silica gel with 70:30 hexane-ethyl acetate.

Workup

  1. temperaturewas refluxed for one hour
  2. temperatureThe solution was cooled
  3. additionpoured onto ice
  4. extractionThe mixture was extracted with ethyl acetate
  5. dissolutionThe solution was dissolved in 60:40 hexane-ethyl acetate
  6. customThe eluate was evaporated
  7. customthe residue was crystallized from 20 mL of hexane

Sources & evidence

ORD record
ord-6394295746ca424e83faad1c3514cbd9
Source dataset
uspto-grants-2002_01
Patent number
US06342503B1

Reaction notes

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