Ethyl Acetate → 3-Chloro-4-[2-(pyrrolidin-1-yl)ethoxy]aniline

HRID 1987903Notes

Reaction equation

HRID 1987903 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.CCOC(C)=O>CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 574214731-[2-(2-chloro-4-nitrophenoxy)ethyl]Pyrrolidine

Product 1

HCID 196269953-Chloro-4-[2-(pyrrolidin-1-yl)ethoxy]aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of Zn powder (620 mg, 9.48 mmol) and 1-(2-(2-chloro-4-nitrophenoxy)ethyl)pyrrolidine (320 mg, 1.19 mmol) in AcOH:H2O (3:1 mL) was heated at 55° C. for 2 h. After cooling the reaction to RT, any solid was removed by filtration and rinsed with AcOH and CH2Cl2. Once the combined filtrate was concentrated using a rotavap, the resulting residue was adjusted pH to 10 with NH4OH and extracted with CH2Cl2 (2×50 mL). The combined organic layers were washed with H2O (10 mL), then dried over MgSO4. After removal of the solvent under vacuum the pale brownish oil (0.26 g, 93%) was carried forward without further purification. MS (ESI) 241 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. customthe reaction to RT
  3. customany solid was removed by filtration
  4. washrinsed with AcOH and CH2Cl2
  5. concentrationOnce the combined filtrate was concentrated
  6. extractionextracted with CH2Cl2 (2×50 mL)
  7. washThe combined organic layers were washed with H2O (10 mL)
  8. dry with materialdried over MgSO4
  9. customAfter removal of the solvent under vacuum the pale brownish oil (0.26 g, 93%)
  10. customwas carried forward without further purification

Sources & evidence

ORD record
ord-e48b39dc231d41adab9b743662822f7b
Source dataset
uspto-grants-2009_06
Patent number
US07553836B2

Reaction notes

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