Hydrochloric Acid → Ethyl 2-(5-amino-2-chlorophenyl)acetate

HRID 1930422Notes

Reaction equation

HRID 1930422 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl>CCO.[Fe]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22970611Ethyl 2-(2-chloro-5-nitrophenyl)acetate

Product 1

HCID 22475346Ethyl 2-(5-amino-2-chlorophenyl)acetateYield 560%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (2.5 g, 44.7 mmol) was added portion wise to a solution of ethyl 2-(2-chloro-5-nitrophenyl)acetate (8 g, 4.68 mmol) and cone. HCl (12 M, 3.9 mL, 46.8 mmol) in EtOH (100 mL). The resultant mixture was heated at 50° C. for 2 hour. The mixture was filtered and the filtrate cake was washed with saturated aqueous Na2CO3 until pH 8. The filter cake was further washed with EtOAc and the combined filtrates were partitioned between EtOAc and water. The organics were dried over Na2SO4 and concentrated in vacuo to provide ethyl 2-(5-amino-2-chlorophenyl)acetate (5.6 g, 56% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.00 (d, J=8.4 Hz, 1 H), 6.50 (s, J=2.8 Hz, 1 H), 6.44 (dd, J=8.4 Hz, 2.8 Hz, 1H), 5.20 (s, 2 H), 4.05 (q, J=7.2 Hz, 2 H), 3.56 (s, 2 H), 1.15 (t, J=7.2 Hz, 3 H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate cake was washed with saturated aqueous Na2CO3 until pH 8
  3. washThe filter cake was further washed with EtOAc
  4. customthe combined filtrates were partitioned between EtOAc and water
  5. dry with materialThe organics were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e236e3831604e98a3791a7297e88057
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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