Hydrochloric Acid → (2-Acetamidophenyl) cyclohexyl methanone

HRID 2379310Notes

Reaction equation

HRID 2379310 reaction equation
[CH:1]1([Mg]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]1[O:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]=1.Cl>CCOCC>[C:10]([NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:16])(=[O:15])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68236AcetanthranilHCID 178419651HCID 178419651, compound

Product 1

HCID 11586813(2-Acetamidophenyl) cyclohexyl methanoneYield 24%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-10 °C

Procedure

Cyclohexylmagnesium bromide (240 ml of a 2M solution in ether, 0.48 mol) in ether (200 ml) was added dropwise to a solution of 2-methyl-4H-3,1-benzoxazin-4-one (100 g, 0.62 mol) in ether (1100 ml) at -10° C. over 2 h. The mixture was stirred at this temperature for 2 h, then at ambient temperature for 30 min. After cooling to -10° C. the suspension was treated with 2M HCl (600 ml), keeping the temperature below 0° C. After stirring for 15 min the layers were separated, and the ethereal layer washed sequentially with water (500 ml), 5% sodium hydroxide solution (2×500 ml) and finally water (2×500 ml). The organic layer was separated, dried (MgSO4), evaporated in vacuo and chromatographed on silica gel using petrol:ethyl acetate (2:1) to give (2-acetamidophenyl) cyclohexyl methanone (28 g, 24%) as a pale yellow solid. mp 66° C. 1H NMR (CDCl3, 360 MHz) δ 1.25-1.89 (10H, m), 2.23 (3H, s), 3.33 (1H, m), 7.13 (1H, d of t, J=6 and 1 Hz), 7.53 (1H, d of t, J=6 and 1 Hz), 7.92 (1H, d, J=6 Hz), 8.76 (1H,d, J=6 Hz), 11.73 (1H, brs).

Workup

  1. waitat ambient temperature for 30 min
  2. customthe temperature below 0° C
  3. stirringAfter stirring for 15 min the layers
  4. customwere separated
  5. washthe ethereal layer washed sequentially with water (500 ml), 5% sodium hydroxide solution (2×500 ml) and finally water (2×500 ml)
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customchromatographed on silica gel

Sources & evidence

ORD record
ord-c5bf5fdda0b64aee861f71f0b45a4a65
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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