4-Aminobenzonitrile → N-(4-Cyanophenyl)glycine

HRID 1527146Notes

Reaction equation

HRID 1527146 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl[CH2:11][C:12]([O-:14])=[O:13].[Na+]>O>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][CH2:11][C:12]([OH:14])=[O:13])=[CH:3][CH:4]=1)#[N:7]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 23665759Sodium chloroacetate

Product 1

HCID 817965N-(4-Cyanophenyl)glycineYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

77.4 g (0.66 mol) of 4-aminobenzonitrile and 150 g (1.31 mol) of sodium chloroacetate were suspended in 1.1 L of water, and the resulting mixture was stirred at reflux temperature for 6.5 hours. After cooling to 0° C., the resulting suspension was stirred at this temperature overnight. The solid was filtered and washed with 200 mL of water. The resulting solid was suspended in 200 mL of ethyl acetate and stirred at room temperature for 1 hour. The solid was filtered, washed with 400 mL of ethyl acetate and dried at 60° C. under vacuum for 5 hours to yield 84.5 g of 2-(4-cyanophenylamino)acetic acid as an off-white solid. Yield: 73.2%. Purity (HPLC, method 3): 98.4%.

Workup

  1. temperatureat reflux temperature for 6.5 hours
  2. stirringthe resulting suspension was stirred at this temperature overnight
  3. filtrationThe solid was filtered
  4. washwashed with 200 mL of water
  5. stirringstirred at room temperature for 1 hour
  6. filtrationThe solid was filtered
  7. washwashed with 400 mL of ethyl acetate
  8. customdried at 60° C. under vacuum for 5 hours

Sources & evidence

ORD record
ord-b2f8b4a0866a4adbbe107fedde532356
Source dataset
uspto-grants-2015_07
Patent number
US09086390B2

Reaction notes

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