3-Nitrobenzoic acid → HCID 723128, compound

HRID 912223Notes

Reaction equation

HRID 912223 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].C(N(C(C)C)C(C)C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:32]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[CH3:33]>[Cl-].[Na+].O.CN(C=O)C>[CH2:32]([N:34]1[CH2:39][CH2:38][N:37]([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:9])[CH2:36][CH2:35]1)[CH3:33]

Participants

7

Reactant 4

HCID 84973-Nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 791961-EthylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 723128HCID 723128, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a DMF solution (10 ml) of 3-nitro-benzoic acid (334 mg) and N-ethyldiisopropylamine (1 ml), HOBt (270 mg) and WSCI (575 mg) were added, followed by stirring at room temperature for 10 minutes. To this, 1-ethyl-piperazine (305 μl) was added, followed by stirring at room temperature for 22 hours. Brine (30 ml) was added, followed by extraction with ethyl acetate (30 ml×2), and the organic layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (dichloromethane/methanol=100/1 to 20/1), to obtain the desired compound (365.3 mg, 69%).

Workup

  1. stirringby stirring at room temperature for 22 hours
  2. extractionfollowed by extraction with ethyl acetate (30 ml×2)
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationAfter the sodium sulfate was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customfollowed by purification by silica gel column chromatography (dichloromethane/methanol=100/1 to 20/1)

Sources & evidence

ORD record
ord-0eff5ab6369447c49e6b4645a67bb992
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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