Ammonia → N-(4-Cyanophenyl)glycine

HRID 919284Notes

Reaction equation

HRID 919284 reaction equation
Cl[CH2:2][C:3]([O-:5])=[O:4].[Na+].[I-].[K+].[NH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+].N.Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([NH:9][CH2:2][C:3]([OH:5])=[O:4])=[CH:11][CH:12]=1)#[N:15]

Participants

9

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 133964-AminobenzonitrileHCID 516892Sodium BicarbonateHCID 23665759Sodium chloroacetate

Product 1

HCID 817965N-(4-Cyanophenyl)glycine

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
87.5 °C

Procedure

Sodium mono chloroacetate (197.42 g), followed by potassium iodide (5 g) and tetrabutyl ammonium bromide (2.5 g) were added to a mixture of 4-aminobenzonitrile (100 g), water (1000 ml) and sodium bicarbonate (42.71 g). The reaction mixture was heated to 85-90° C. and stirred for 24 hours. The reaction mixture was cooled to 25-30° C. and treated with ammonia followed by hydrochloric acid. Filtered the solid, washed with water and then dried to get title compound.

Workup

  1. temperatureThe reaction mixture was cooled to 25-30° C.
  2. filtrationFiltered the solid
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-dd24db35014a43cf820de8b964dfd531
Source dataset
uspto-grants-2016_03
Patent number
US09273030B2

Reaction notes

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