Dichloromethane → N-Nitroaniline

HRID 1790715Notes

Reaction equation

HRID 1790715 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5](O)=[CH:4][C:3]=1[N+:9]([O-])=O.NC1C=CC(OC2C=CN=C(C(NC)=O)C=2)=CC=1[N+:30]([O-:32])=[O:31].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>COCCOC.O.O.C(OCC)(=O)C>[N+:30]([NH:9][C:3]1[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=1)([O-:32])=[O:31]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 37588824-Amino-3-NitrophenolHCID 177564974-(4-amino-3-nitrophenoxy)-N-methylpicolinamide

Product 1

HCID 61191N-Nitroaniline

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5 (1 eq), 6 (1 eq), and sodium carbonate (1.2 eq) in DME/H2O (3:1) was degassed by bubbling argon through the solution for 10 minutes. Pd(II)(dppf)Cl2.MeCl2 (0.1 eq) was added to the reaction solution and the reaction was sealed. The reaction was heated at 100° C. overnight. The reaction was cooled to RT and ethyl acetate and water were added. The organic layer was separated from the aqueous layer. The aqueous layer was washed once more with ethyl acetate. The organic layers were combined, dried (Na2SO4), and concentrated under vacuum to yield the desired product 7. MS: MH+=469

Workup

  1. customby bubbling argon through the solution for 10 minutes
  2. customthe reaction was sealed
  3. temperatureThe reaction was cooled to RT
  4. customThe organic layer was separated from the aqueous layer
  5. washThe aqueous layer was washed once more with ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8f82121579ef4eca9d6cf6b432beefbd
Source dataset
uspto-grants-2006_07
Patent number
US07071216B2

Reaction notes

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