4-Aminophenylacetonitrile → HCID 59717854, compound

HRID 2197634Notes

Reaction equation

HRID 2197634 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Cl[C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=1>CO.C(OCC)(=O)C>[C:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=2)=[CH:3][CH:4]=1)#[N:10]

Participants

5

Reactant 2

HCID 770004-AminophenylacetonitrileHCID 804566-Chloronicotinamide

Product 1

HCID 59717854HCID 59717854, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 4-aminophenylacetonitrile (5.0 g, 37.9 mmol) and 6-chloro-nicotinamide (6.3 g, 40.3 mmol) in a flask and heat at 150° C. for 5 hours. Cool, dissolve the residue in methanol, dilute with ethyl acetate, then wash with saturated aqueous sodium bicarbonate solution. Dry the organic layer over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield the crude product (10 g). The crude product was purified by flash column chromatography on silica gel eluting with 10% aqueous ammonium hydroxide in ethanol and chloroform to yield 6-(4-cyanomethyl-phenylamino)-nicotinamide. Triturate the resulting solid with hot isopropanol, collect the precipitate to yield 6-(4-cyanomethyl-phenylamino)-nicotinamide (1.8 g): 1H NMR (DMSO-D6, 300.00 MHz): 9.48 (s, 1H), 8.69 (d, 1H, J=2.1 Hz), 8.03-7.71 (m, 4H), 7.31-7.21 (m, 3H), 6.85 (d, 1H, J=8.8 Hz), 3.97 (s, 2H).

Workup

  1. temperatureCool
  2. washwash with saturated aqueous sodium bicarbonate solution
  3. dry with materialDry the organic layer over sodium chloride/magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customto yield the crude product (10 g)
  7. customThe crude product was purified by flash column chromatography on silica gel eluting with 10% aqueous ammonium hydroxide in ethanol and chloroform

Sources & evidence

ORD record
ord-22fd5ec9c1b34deabc5bdd8838e757f9
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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