Water → HCID 19026965, compound

HRID 1032963Notes

Reaction equation

HRID 1032963 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].N1C=CC=CC=1.[C:16](Cl)(=[O:19])[CH:17]=[CH2:18].O>C(Cl)Cl>[C:16]([NH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9])(=[O:19])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 72642-Amino-4-methylphenolHCID 13140Acryloyl chloride

Product 1

HCID 19026965HCID 19026965, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-4-methylphenol (5 g, 40.6 mmol) and pyridine (5 ml, 62 mmol) in methylene chloride (70 ml) was added dropwise a solution of acryloyl chloride (4 ml, 50 mmol) in methylene chloride (30 ml) under ice-cooling. The reaction mixture was stirred at 0° C. for 2 hours. To the reaction mixture was added water, and the mixture was stirred at room temperature for 30 minutes, extracted with methylene chloride, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off, and thus obtained brown oil was purified by column chromatography on silica gel to give a pale yellow prismatic crystals. Yield 1.55 g (22%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. extractionextracted with methylene chloride
  4. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthus obtained brown oil was purified by column chromatography on silica gel
  8. customto give a pale yellow prismatic crystals

Sources & evidence

ORD record
ord-93e36a3f93d645b086393a8f61617ea4
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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