Water → 2-Methyl-5-(2-methyl-1,3-dioxolan-2-yl)aniline

HRID 1893535Notes

Reaction equation

HRID 1893535 reaction equation
O.[C:2]1([CH3:8])C=CC=CC=1.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:18])=[O:17])=[CH:12][C:11]=1[N+:19]([O-])=O.C1(C)C=CC(S(O)(=O)=[O:29])=CC=1>C(O)CO>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([CH3:18])[O:29][CH2:2][CH2:8][O:17]2)=[CH:12][C:11]=1[NH2:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 792463'-Nitro-4'-methylacetophenone

Product 1

HCID 668820662-Methyl-5-(2-methyl-1,3-dioxolan-2-yl)anilineYield 94%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a flask mounted with Dean-Stark water removing apparatus (Dean-Stark trap) were added toluene (200 ml), 4-methyl-3-nitroacetophenone (9.77 g, 54.53 mmol), ethylene glycol (4.6 ml) and p-toluenesulfonic acid.monohydrate (0.79 g), and the mixture was heated under reflux for 100 min. The reaction mixture was cooled, washed with diluted aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give a crude brown oil (13.0 g). Using the crude oil and according to the method of Reference Example 61, step B, the title compound (9.89 g, yield 94%) was obtained as a pale-yellow solid.

Workup

  1. temperatureunder reflux for 100 min
  2. temperatureThe reaction mixture was cooled
  3. washwashed with diluted aqueous sodium hydroxide solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe solution was concentrated under reduced pressure
  7. customto give a crude brown oil (13.0 g)

Sources & evidence

ORD record
ord-9798094bdea14ce180d24232641e453d
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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