Hydrochloric Acid → HCID 90016662, compound

HRID 1054999Notes

Reaction equation

HRID 1054999 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.OO.O.C(=O)(O)[O-].[Na+].[ClH:21]>>[Cl:21][C:3]1[CH:4]=[C:5]([C:9]([F:12])([F:10])[F:11])[C:6]([NH2:8])=[N:7][C:2]=1[CH3:1]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 516892Sodium BicarbonateHCID 90018297HCID 90018297, compound

Product 1

HCID 90016662HCID 90016662, compoundYield 99.2%

Procedure

6-Methyl-3-(trifluoromethyl)pyridin-2-amine (59 mg, 335 μmol, Eq: 1.00) was suspended in 37% HCl aq (4.13 ml) and 35% hydrogen peroxide aq (488 mg, 440 μl, 5.02 mmol, Eq: 15) was added dropwise. The mixture was stirred for 20 min. Water (50 ml) was added. The mixture was alkalized by addition of sodium bicarbonate and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to an oil. The product (70 mg, 99.2%) was obtained as a light yellow solid by column chromatography (SiO2, ethyl acetate/n-heptane). MS: m/z=211.2 (M+H+)

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-cc9f7045ef03467297544f3aba179931
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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