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

HRID 392972Notes

Reaction equation

HRID 392972 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>C(#N)C>[CH:15]1([NH:21][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 2972846Methyl 4-(cyclohexylamino)-3-nitrobenzoateYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 4-chloro-3-nitrobenzoate (5.00 g, 23.2 mmol), cylohexylamine (3.98 mL, 34.8 mmol), and triethylamine (4.8 ML, 35 mmol) in acetonitrile (75 mL) was reluxed for 22 h under an argon atmosphere. The reaction mixture was concentrated to a volume of ˜20 mL and the precipitated solid was filtered. The filtrate was diluted with ethyl acetate and was washed with 1M citric acid (1×) followed by saturated NaHCO3 (1×). The organic layer was dried (MgSO4) and concentrated on a rotary evaporator. The residue was purified by column chromatography (silica gel, 50-70% dichloromethane/hexanes (v/v)) to give compound 45 as a yellow solid (6.32 g, 98%). ESI-MS m/e 279.2 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to a volume of ˜20 mL
  2. filtrationthe precipitated solid was filtered
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwas washed with 1M citric acid (1×)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated on a rotary evaporator
  7. customThe residue was purified by column chromatography (silica gel, 50-70% dichloromethane/hexanes (v/v))

Sources & evidence

ORD record
ord-45deda20525d4777a3e22e44a58476bc
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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