Hydrochloric Acid → 2-(4-Acetamino-3-methylphenyl)benzonitrile

HRID 976589Notes

Reaction equation

HRID 976589 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(N(CC)CC)C.[C:26](OC(=O)C)(=[O:28])[CH3:27].Cl>C(OCC)(=O)C.CN(C)C1C=CN=CC=1.[Pd]>[NH:8]([C:7]1[CH:6]=[CH:5][C:4]([C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])=[CH:3][C:2]=1[CH3:1])[C:26]([CH3:27])=[O:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 214689052-(3-Methyl-4-nitrophenyl)benzonitrile

Product 1

HCID 214688382-(4-Acetamino-3-methylphenyl)benzonitrileYield 51%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Methyl-4-nitrophenyl)benzonitrile (6.3 moles, 1.5 g) was hydrogenated in ethyl acetate (50 ml) over 5% Pd/C (0.50 g). The catalyst was filtered, and the solution concentrated to an oil. The oil was dissolved in 10 ml of methylene chloride and triethylamine (9.4 mmoles, 1.4 ml). Acetic anhydride (9.4 mmoles, 0.960 g) and 4-dimethylaminopyridine (50 mg) were added. The reaction was stirred for 1 hour and poured into 20 ml of 5N HCl. The organic phase was washed with saturated sodium bicarbonate solution, dried over sodium sulfate, and concentrated. The product was crystallized from ether and hexane to yield 1.2 g of 2-(4-acetamino-3-methylphenyl)benzonitrile. (MS)

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe solution concentrated to an oil
  3. dissolutionThe oil was dissolved in 10 ml of methylene chloride
  4. washThe organic phase was washed with saturated sodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was crystallized from ether and hexane

Sources & evidence

ORD record
ord-173fbb0876e54fe7a89f50230ca8873f
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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