Pyridine → Methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate

HRID 732645

Reaction equation

HRID 732645 reaction equation
[C:1](Cl)(=[O:12])[O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.ClCCl.[NH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1[Cl:28].N1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:28][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:18]=1[NH:17][C:1]([O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)=[O:12])[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 821294-Nitrophenyl chloroformateHCID 1515284Methyl 4-Amino-3-chlorobenzoate

Product 1

HCID 59178754Methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 3.5 g portion of 4-nitrophenyl chlorocarbonate was added at 0° C. to a 30 ml dichloromethane suspension of 3 g of methyl 4-amino-3-chlorobenzoate and 4 ml of pyridine and stirred at room temperature for 2Hours. The reaction solution was diluted with chloroform and washed with 1 M hydrochloric acid, water, saturated sodium bicarbonate aqueous solution, water and saturated brine in that order, and the organic layer was dried with anhydrous sodium sulfate. This was concentrated under a reduced pressure, and the thus obtained residue was recrystallized from hexane-ethyl acetate to obtain 4.23 g of methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate as a pale brown powder.

Workup

  1. washwashed with 1 M hydrochloric acid, water, saturated sodium bicarbonate aqueous solution, water and saturated brine in that order
  2. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  3. concentrationThis was concentrated under a reduced pressure
  4. customthe thus obtained residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-5af8aeb32cf54573a24ddac1c50705c3
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Linked notes

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