Formic Acid → N-(2-adamantyl)-2,6-dimethoxy-4-methylaniline

HRID 2920

Reaction equation

HRID 2920 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([O:11][CH3:12])[C:4]=1[NH2:5].C(O)=O.[CH:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[C:17]1=O)[CH2:23]2>C1(C)C=CC=CC=1>[CH:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH:17]1[NH:5][C:4]1[C:6]([O:11][CH3:12])=[CH:7][C:8]([CH3:10])=[CH:9][C:3]=1[O:2][CH3:1])[CH2:23]2

Participants

5

Reactant 3

HCID 284Formic AcidHCID 64151AdamantanoneHCID 124090902,6-Dimethoxy-4-methylaniline

Product 1

HCID 18936508N-(2-adamantyl)-2,6-dimethoxy-4-methylanilineYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2.1 g of 2,6-dimethoxy-4-methylaniline are dissolved in 10 ml of toluene, 0.5 ml of formic acid is then added to this solution and the mixture is heated to gentle reflux, under inert atmosphere, and 0.93 g of 2-adamantanone, dissolved in 10 ml of toluene, is added dropwise at this temperature. The reaction mixture is heated at reflux for 48 hours, is then evaporated to dryness and the residue is taken up in 30 ml of 2N hydrochloric acid. The insoluble white crystals are filtered and discarded. The acidic filtrate is extracted with dichloromethane. The organic extracts are washed with a 5% aqueous sodium bicarbonate solution and then with water and the organic phases are then dried over anhydrous sodium sulphate. Evaporation leaves a colourless residue which is purified by flash chromatography on a column of silica gel, eluent: toluene/ethyl acetate 7/3 (v/v) in order to obtain N-(2-adamantyl)-2,6-dimethoxy-4-methylaniline; M.p.=100° C., Yield 52%.

Workup

  1. additionis added dropwise at this temperature
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 48 hours
  4. customis then evaporated to dryness
  5. filtrationThe insoluble white crystals are filtered
  6. extractionThe acidic filtrate is extracted with dichloromethane
  7. washThe organic extracts are washed with a 5% aqueous sodium bicarbonate solution
  8. dry with materialwith water and the organic phases are then dried over anhydrous sodium sulphate
  9. customEvaporation
  10. customleaves a colourless residue which
  11. customis purified by flash chromatography on a column of silica gel, eluent

Sources & evidence

ORD record
ord-a85fcfa6da084f02a5caf57a4c6ff853
Source dataset
uspto-grants-1998_03
Patent number
US05731340

Linked notes

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