Aniline → HCID 86670006, compound

HRID 1401124Notes

Reaction equation

HRID 1401124 reaction equation
O=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1CCCCC1>[C:11]1([NH:10]/[C:2](/[CH2:8][CH3:9])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 121699Methyl 3-oxovalerate

Product 1

HCID 86670006HCID 86670006, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8078CyclohexaneSolvent

Procedure

A mixture of methyl 3-oxovalerate (5.21 g, 40.0 mmol), aniline (3.66 mL, 40.0 mmol), p-toluenesulfonic acid monohydrate (533 mg, 2.80 mmol) and cyclohexane (25 mL) was stirred with heating under reflux for 2 hr. The mixture was concentrated under reduced pressure, the insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=98:2→94:6) to give the title compound (5.93 g, 72%) as a colorless oil.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe insoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=98:2→94:6)

Sources & evidence

ORD record
ord-7575bccfb1ad45adb0e82c4860fae14b
Source dataset
uspto-grants-2014_12
Patent number
US08907089B2

Reaction notes

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