Dinitrofluorobenzene → 3-(2-Aminobenzoyl)-2-(2,4-dinitroanilino)propanoic acid

HRID 1877343Notes

Reaction equation

HRID 1877343 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([NH2:15])=[C:5]([C:7]([CH2:9][C@H:10]([NH2:14])[C:11]([OH:13])=[O:12])=[O:8])[CH:6]=1.[N+:16]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1F)([O-:18])=[O:17].C([O-])(O)=O.[Na+]>C(O)C>[NH2:15][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[C:7]([CH2:9][CH:10]([NH:14][C:20]1[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=1[N+:16]([O-:18])=[O:17])[C:11]([OH:13])=[O:12])=[O:8]

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 161166KynurenineHCID 516892Sodium Bicarbonate

Product 1

HCID 112802543-(2-Aminobenzoyl)-2-(2,4-dinitroanilino)propanoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

L-Kynurenine (125 mg) is dissolved in 5 cc of absolute ethanol in a 50 cc flask. A solution of 2,4-dinitrofluorobenzene, 71 mg in EtOH 5 cc is then added (a clear yellow solution is formed). After five minutes, 2 cc of a 10% NaHCO3 solution are introduced drop-wise in the flask. The reaction is left at room temperature overnight. The following morning the formed light yellow precipitate is filtered, washed with water and ethanol and dried in UHV obtaining 80 mg of product (approx. yield 71%).

Workup

  1. customis formed)
  2. waitThe reaction is left at room temperature overnight
  3. filtrationThe following morning the formed light yellow precipitate is filtered
  4. washwashed with water and ethanol
  5. customdried in UHV

Sources & evidence

ORD record
ord-4ae749a44c1b47d488d85366baef0a30
Source dataset
uspto-grants-2012_11
Patent number
US08309767B2

Reaction notes

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