Sulfuric Acid → HCID 90112540, compound

HRID 1508755Notes

Reaction equation

HRID 1508755 reaction equation
S(=O)(=O)(O)[OH:2].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[C:9]([CH3:16])[CH:8]=1>C(=O)(O)[O-].[Na+]>[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH2:15])=[O:2])=[C:9]([CH3:16])[CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 53446539HCID 53446539, compound

Product 1

HCID 90112540HCID 90112540, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Sulfuric acid (26 mL) was added to 2-(4-amino-2-methylphenyl)acetonitrile (0.500 g, 3.42 mmol) at 0° C. The mixture was warmed to rt for 4 h, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and concentrated to afford the title compound (0.252 g, 50%) as a tan solid. MW=164.20. 1H NMR (DMSO-d6, 500 MHz) δ 7.09 (s, 1H), 6.81 (d, J=7.9 Hz, 1H), 6.74 (s, 1H), 6.39-6.35 (m, 1H), 6.33-6.29 (m, 1H), 4.78 (s, 2H), 3.19 (s, 2H), 2.10 (s, 3H); APCI MS m/z 165 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-65ddb4b061994673aaadfdbce30d0d79
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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