Chloroacetic Acid → Glycine, N-(4-nitrophenyl)-

HRID 1373077Notes

Reaction equation

HRID 1373077 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]([OH:15])=[O:14]>O>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 74754-Nitroaniline

Product 1

HCID 12095Glycine, N-(4-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4-nitroaniline (13.8 g, 100 mmol) in water (300 mL) was added chloroacetic acid (18.9 g, 200 mmol). The reaction mixture was refluxed overnight and cooled to rt. The title compound was collected by filtration, washed with water and a mixture of hexane and ether (1:1) and dried in vacuo to yield 14.6 g (74%). 1H NMR (400 MHz, DMSO-d6) δ: 12.83 (s, 1H), 8.00 (d, 2H), 7.45 (t, 1H), 6.65 (d, 2H), 4.00 (d, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationThe title compound was collected by filtration
  3. washwashed with water
  4. additiona mixture of hexane and ether (1:1)
  5. customdried in vacuo
  6. customto yield 14.6 g (74%)

Sources & evidence

ORD record
ord-7d550b77efa54bcfa87997cf355b8852
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

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