Dichloromethane → HCID 68511467, compound

HRID 1929335Notes

Reaction equation

HRID 1929335 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=1.[OH-].[Na+].ClCCl>CO.C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:13])[C:9]([NH2:10])=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 68512351HCID 68512351, compound

Product 1

HCID 68511467HCID 68511467, compoundYield 87.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

add 1.75 g of iron powder to a solution of 1.4 g of 4-[(2,6-dichlorobenzyl)oxy]-2-nitroaniline in 80 cm3 of methanol and 7 cm3 of glacial acetic acid. The reaction mixture is refluxed for three hours. The mixture is concentrated under reduced pressure (0.2 kPa). The residue is taken up in 30 cm3 of water and the pH of the suspension thus obtained is adjusted to 10-11 by adding 2N aqueous solution of sodium hydroxide; 350 cm3 of dichloromethane is then added. After vigorous stirring for 15 min, the insoluble matter is filtered. The filtrate is decanted, then the organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure (0.2 kPa). We obtain 1.11 g of 4-[(2,6-dichlorobenzyl)oxy]benzene-1,2-diamine in the form of a black resin, which has the following characteristics:

Workup

  1. temperatureThe reaction mixture is refluxed for three hours
  2. concentrationThe mixture is concentrated under reduced pressure (0.2 kPa)
  3. customthe pH of the suspension thus obtained
  4. filtrationthe insoluble matter is filtered
  5. customThe filtrate is decanted
  6. dry with materialthe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure (0.2 kPa)

Sources & evidence

ORD record
ord-7fa367a22c1c4fe5be92e0052149fade
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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