Hydrochloric Acid → 2-Isopropyl-5-methyl-cyclohexanecarboxylic acid (4-methoxy-2-nitrophenyl)-amide

HRID 1916896Notes

Reaction equation

HRID 1916896 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[CH:13]1([CH3:25])[CH2:18][CH2:17][CH:16]([CH:19]([CH3:21])[CH3:20])[CH:15]([C:22](Cl)=[O:23])[CH2:14]1.C(Cl)Cl.Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:22]([CH:15]2[CH2:14][CH:13]([CH3:25])[CH2:18][CH2:17][CH:16]2[CH:19]([CH3:21])[CH3:20])=[O:23])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 667934-Methoxy-2-nitroanilineHCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

Product 1

HCID 668315102-Isopropyl-5-methyl-cyclohexanecarboxylic acid (4-methoxy-2-nitrophenyl)-amideYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

4-Methoxy-2-nitroaniline (5 g, 0.018 mol) was dissolved in pyridine (50) and treated with menthoyl chloride (3.57 g, 0.018 mol). The reaction mixture was heated to 50° C. and stirred vigorously for 6 h. The reaction mixture was cooled to room temperature and poured into a mixture of CH2Cl2 (100 mL) and 1N HCl (100 mL)). The heterogeneous mixture was transferred to a reparatory funnel where the aqueous phase was separated and re-extracted with CH2Cl2 (2×100 mL). The organic phases were combined and washed with 1N HCl (8×100 mL), H2O (1×100 mL), 1N NaOH (2×100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (20 to 50% ethyl acetate/hexane for elution) provided the title compounds as colorless solid (4.9 g, 83%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe heterogeneous mixture was transferred to a reparatory funnel
  3. customwhere the aqueous phase was separated
  4. extractionre-extracted with CH2Cl2 (2×100 mL)
  5. washwashed with 1N HCl (8×100 mL), H2O (1×100 mL), 1N NaOH (2×100 mL), brine (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (20 to 50% ethyl acetate/hexane for elution)

Sources & evidence

ORD record
ord-fe9f5886239640638b9dee680ce807a2
Source dataset
uspto-grants-2013_12
Patent number
US08618155B2

Reaction notes

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