Sulfuric Acid → HCID 178428836, compound

HRID 1253835Notes

Reaction equation

HRID 1253835 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3=[N:14][C:15]([CH3:19])=[CH:16][C:17](N)=[C:12]3[C:11]([CH3:20])=[CH:10]2)=[C:4]([CH3:21])[CH:3]=1.[OH:22]S(O)(=O)=O.N([O-])=O.[Na+].C([O-])(O)=O.[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:19])[CH:16]=[C:17]([OH:22])[C:12]=3[C:11]([CH3:20])=[CH:10]2)=[C:4]([CH3:21])[CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 60035418HCID 60035418, compound

Product 1

HCID 178428836HCID 178428836, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

With ice-cooling, to a suspension of 1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-ylamine (17.9 g) in a mixture of 1,4-dioxane (45 mL) and water (45 mL) was added dropwise a mixture of concentrated H2SO4 (17.8 mL) and water (90 mL) and then a solution of NaNO2 (6.2 g) in water (62 mL). The mixture was stirred at room temperature for 20 minutes, and heated at 100° C. for 1.5 hours. After cooling in an ice-cooling bath, the reaction mixture was poured into a cold saturated NaHCO3 aqueous solution and extracted with CHCl3. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give a solid. The solid was washed with a mixture of ethyl acetate and diisopropylether (1:5) to give 1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-ol (14.4 g).

Workup

  1. additionwas added dropwise
  2. temperatureheated at 100° C. for 1.5 hours
  3. temperaturecooling bath
  4. extractionextracted with CHCl3
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give a solid
  9. washThe solid was washed with a mixture of ethyl acetate and diisopropylether (1:5)

Sources & evidence

ORD record
ord-4f19c32557534b6d9a289496a82026e2
Source dataset
uspto-grants-2013_06
Patent number
US08455511B2

Reaction notes

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