Cyclohexylamine → Ethyl 4-(cyclohexylamino)-3-nitrobenzoate

HRID 2068283Notes

Reaction equation

HRID 2068283 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:16]1([NH:22][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 5298559Ethyl 4-(cyclohexylamino)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Ethyl 4-fluoro-3-nitrobenzoate (5.73 g, 0.0269 mol) was dissolved in 25 mL of DMF. While stirring under an atmosphere of nitrogen, cyclohexanamine in 5 mL of DMF (3.4 mL, 0.030 mol) and N,N-diisopropylethylamine (14 mL, 0.080 mol) were added simultaneously via two seperate syringes. The reaction mixture turned immediately into a deep yellow/orange gel and was diluted with another 5 mL of DMF. The reaction mixture was slightly exothermic and stirring was maintained until the reaction was complete as determined by LC/MS. The reaction mixture was then diluted with ethyl acetate and washed with 5% citric acid then brine. The organic phase was collected, dried over sodium sulfate and concentrated to a yellow oil which solidified under high vacuum to yield 8.47 g of the title compound.

Workup

  1. customseperate syringes
  2. additionwas diluted with another 5 mL of DMF
  3. stirringstirring
  4. temperaturewas maintained until the reaction
  5. additionThe reaction mixture was then diluted with ethyl acetate
  6. washwashed with 5% citric acid
  7. customThe organic phase was collected
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to a yellow oil which

Sources & evidence

ORD record
ord-e3e2ef8a006f4a46868be24c8d42c6a2
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

Loading…