Chloroacetic Acid → N-(4-Cyanophenyl)glycine

HRID 1373074Notes

Reaction equation

HRID 1373074 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]([OH:14])=[O:13]>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 300Chloroacetic AcidHCID 133964-Aminobenzonitrile

Product 1

HCID 817965N-(4-Cyanophenyl)glycineYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-aminobenzonitrile (12 g, 101.6 mmol) and chloroacetic acid (20 g, 211.6 mmol) in water (250 mL) was refluxed until the product began to separate out. After cooled down to the room temperature, the solids were collected by filtration, washed with ether, and dried in vacuo to afford 10.35 g (58%) of the title compound which was pure enough for the next reaction. 1H NMR (400 MHz, DMSO-d6) δ 12.73 (s, 1H), 7.46 (dd, 2H), 6.93 (t, 1H), 6.65 (dd, 2H), 3.91 (d, 2H).

Workup

  1. customto separate out
  2. filtrationthe solids were collected by filtration
  3. washwashed with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4aeab88d6fcd4cbe970360075ad60530
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

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