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

HRID 1527150Notes

Reaction equation

HRID 1527150 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+].C(=O)(O)[O-].[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

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 516892Sodium BicarbonateHCID 23665759Sodium chloroacetate

Product 1

HCID 817965N-(4-Cyanophenyl)glycineYield 70.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

54.0 g (0.46 mol) of 4-aminobenzonitrile and 107.2 g (0.92 mol) of sodium chloroacetate were suspended in 730 mL of water, and the resulting mixture was stirred at reflux temperature for 4 hours. After cooling to room temperature, pH was adjusted to 8-9 with sodium bicarbonate. The resulting solution was washed with 2×200 mL of ethyl acetate, and 5M hydrochloric acid was added to the aqueous phase until pH=3. The precipitated solid was isolated by filtration, washed with 100 mL of water and dried to yield 57.1 g of 2-(4-cyanophenylamino)acetic acid as an off-white solid. Yield: 70.9%. Purity (HPLC, method 3): 92.9%.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. washThe resulting solution was washed with 2×200 mL of ethyl acetate, and 5M hydrochloric acid
  3. additionwas added to the aqueous phase until pH=3
  4. customThe precipitated solid was isolated by filtration
  5. washwashed with 100 mL of water
  6. customdried

Sources & evidence

ORD record
ord-c3acf9d5cde7406aa952678df8caf37c
Source dataset
uspto-grants-2015_07
Patent number
US09086390B2

Reaction notes

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