Bicarbonate Ion → HCID 67283381, compound

HRID 1253817Notes

Reaction equation

HRID 1253817 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([NH2:12])=[CH:5][CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1.[F:13][C:14]([F:19])([F:18])[C:15](O)=O.C(=O)(O)[O-]>Cl.C(Cl)Cl>[CH3:1][N:2]1[C:3]2[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=2[N:12]=[C:15]1[C:14]([F:19])([F:18])[F:13]

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 6422Trifluoroacetic acidHCID 21956374N~2~-Methyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 67283381HCID 67283381, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A 250 ml round bottomed flask was charged with N1-methyl-5-nitrobenzene-1,2-diamine (29 g, 0.16 mol), trifluoroacetic acid (22 ml, 0.24 mol) and a few drops of concentrated HCl. A minimum amount of DCM (˜20 ml) was added so that the solid mixture was stirring. The reaction mixture was heated to 70° C. for 12 hours forming a dark brown liquid. The reaction mixture was allowed to cool to room temperature, basified by the slow addition of saturated bicarbonate solution, and extracted into ethyl acetate. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The compound was purified by flash column chromatography (10 to 20% ethyl acetate/petrol) to afford the title compound (8 g, 20% yield). 1H NMR (DMSO D6, 400 MHz) 4.2 (3H, s), 8.05 (1H, d), 8.35 (1H, d), 8.55 (1H, s); MS (ES+) 246.

Workup

  1. customforming a dark brown liquid
  2. temperatureto cool to room temperature
  3. extractionextracted into ethyl acetate
  4. extractionThe aqueous layer was further extracted twice with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe compound was purified by flash column chromatography (10 to 20% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-03878b387a8341e5b0be38436a5f0fdf
Source dataset
uspto-grants-2013_06
Patent number
US08455507B2

Reaction notes

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