Ethyl Bromide → 5-(Ethylamino)-2-methylphenol

HRID 1415078Notes

Reaction equation

HRID 1415078 reaction equation
[CH2:1](Br)[CH3:2].[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[CH2:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 10340Sodium CarbonateHCID 178185-Amino-2-methylphenol

Product 1

HCID 158012485-(Ethylamino)-2-methylphenol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

88.6 gm of ethyl bromide were added to a solution of 50 gm of 5-amino-2-methylphenol in 250 ml of ethanol; and the mixture was refluxed for four hours. After the solution had cooled, it was diluted with 1.2 liters of water and was made weakly alkaline with sodium carbonate. After repeated extraction with ether, the ether extracts were dried and concentrated. The residue was recrystallized from ethanol, and had a melting point of 128° C to 129° C.

Workup

  1. temperatureand the mixture was refluxed for four hours
  2. temperatureAfter the solution had cooled
  3. extractionextraction with ether
  4. dry with materialthe ether extracts were dried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-2d62aeab36f94fec92bdcf214f0008ec
Source dataset
uspto-grants-1977_01
Patent number
US04003699

Reaction notes

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