Ethyl 2-(3,4-dichloroanilino)acetate → N-(3,4-dichlorophenyl)glycine

HRID 1373075Notes

Reaction equation

HRID 1373075 reaction equation
C([O:3][C:4](=[O:15])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)C>Cl>[Cl:14][C:9]1[CH:8]=[C:7]([NH:6][CH2:5][C:4]([OH:15])=[O:3])[CH:12]=[CH:11][C:10]=1[Cl:13]

Participants

3

Reactant 1

HCID 2727804Ethyl 2-(3,4-dichloroanilino)acetate

Product 1

HCID 351250N-(3,4-dichlorophenyl)glycineYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The suspension of (3,4-dichloro-phenylamino)-acetic acid ethyl ester (0.38 g, 1.5 mmol) in 10% HCl (7 mL) was refluxed for 4 h. Water was removed under reduced pressure and the resulting solids were collected by filtration, washed with ether, and dried in vacuo to afford 0.33 g (84%) of the title compound as its hydrochloride salt. 1H-NMR (400 MHz, DMSO-d6) δ: 7.26 (d, 1H), 6.75 (d, 1H), 6.56 (d, 1H), 5.85 (brs, 2–3H), 3.83 (s, 2H).

Workup

  1. temperaturewas refluxed for 4 h
  2. customWater was removed under reduced pressure
  3. filtrationthe resulting solids were collected by filtration
  4. washwashed with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-1939edccaccb453d926dc8ba1bc627fb
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

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