2-Amino-4-methylphenol → HCID 178426743, compound

HRID 41330

Reaction equation

HRID 41330 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=O.[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>O.C(Cl)Cl>[O:9]([C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1/[N:1]=[CH:16]/[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=1)[C:20]1[CH:19]=[CH:18][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 72642-Amino-4-methylphenolHCID 8058HexaneHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 178426743HCID 178426743, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
-35 °C

Procedure

To a slurry of 2-amino-4-methylphenol (4.40 g, 35.7 mmol) in 300 mL water, a water solution of pyridine-2-carbaldehyde (3.80 g, 35.5 mmol) was slowly added, forming a yellow slurry. After stirring overnight, the suspension was poured through a frit and the solid washed with water. The orange solid was dissolved in 300 mL CH2Cl2 and extracted with 3×100 mL water, dried over MgSO4 and filtered to give a red solution. The solvent was removed under vacuum to give a red oil. The oil was re-dissolved in CH2Cl2, layered with an equal volume of hexane and cooled to −35° C. to yield yellow crystals of 11(5.56 g, 73% yield).

Workup

  1. customforming a yellow slurry
  2. additionthe suspension was poured through a frit
  3. washthe solid washed with water
  4. dissolutionThe orange solid was dissolved in 300 mL CH2Cl2
  5. extractionextracted with 3×100 mL water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customto give a red solution
  9. customThe solvent was removed under vacuum
  10. customto give a red oil

Sources & evidence

ORD record
ord-346124835bb6415c9c0a227b1352a1d6
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Linked notes

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