2-Amino-4-methylphenol → 35875-76-4

HRID 1506816Notes

Reaction equation

HRID 1506816 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.[C:10](OC1C=CC=CC=1)(=O)[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13]>C(O)C>[OH:13][C:12]1[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=1[C:10]1[O:8][C:7]2[CH:6]=[CH:5][C:4]([CH3:9])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 72642-Amino-4-methylphenolHCID 8361Phenyl Salicylate

Product 1

HCID 441536535875-76-4

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2-amino-p-cresol (10.0 g, 0.081 mole) and phenyl salicylate (17.4 g, 0.08 mole) was heated under nitrogen atmosphere in an oil bath at 200° C. for 1½ h. To the cooled reaction mixture ethanol was added and the product filtered off under suction. The product was dried under vacuum at 75° C., and then purified by column chromatography (dichloromethane). The eluent containing the product was concentrated and ethanol added to the residue to give a bright white crystalline solid. The product was suction filtered and dried under vacuum at 75° C. Yield 7.4 g (40%). M.p 138° C. (DSC, onset). Elemental analysis: Found, C 74.62, H 4.86 and N 6.32%. C14H11NO2 requires C 74.65, H 4.92 and N 6.22%.

Workup

  1. additionwas added
  2. filtrationthe product filtered off under suction
  3. customThe product was dried under vacuum at 75° C.
  4. custompurified by column chromatography (dichloromethane)
  5. additionThe eluent containing the product
  6. concentrationwas concentrated
  7. additionethanol added to the residue
  8. customto give a bright white crystalline solid
  9. filtrationfiltered
  10. customdried under vacuum at 75° C
  11. customM.p 138° C. (DSC, onset)

Sources & evidence

ORD record
ord-b769349b5d444f6d910e2688b79d0e9a
Source dataset
uspto-grants-2015_12
Patent number
US09221770B2

Reaction notes

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