Pyridine → HCID 228606, compound

HRID 722105Notes

Reaction equation

HRID 722105 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1N.[C:10](Cl)([CH3:12])=[O:11].[N:14]1C=CC=CC=1>>[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[CH2:12][C:10]([NH2:14])=[O:11]

Participants

4

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 118442,3-Dichloroaniline

Product 1

HCID 228606HCID 228606, compound

Procedure

A solution of 2,3-dichloroaniline (5.00 g, 30.86 mmol) in pyridine (20 ml) was cooled to 0° C. and treated with AcCl (4.85 g, 62 mmol). The reaction mixture was stirred at r.t. for 1 h and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with 1% aqueous hydrochloric acid, water and brine, and dried over MgSO4. The solution was concentrated and recrystallized from EtOAc/hexane to give (2,3-dichloro-phenyl)-acetamide (4.50 g, 22 mmol). HPLC Rt: 5.52 min. 1H-NMR (CDCl3): δ 8.35 (br. s, 1H), 7.7 (1H), 7.24 (1H), 7.23 (1H), 2.28 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1% aqueous hydrochloric acid, water and brine
  4. dry with materialdried over MgSO4
  5. concentrationThe solution was concentrated
  6. customrecrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-be65856a93154502a9156d28c799b91a
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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