4-Nitroanthranilic acid → HCID 11120008, compound

HRID 1531730Notes

Reaction equation

HRID 1531730 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:13])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=O)([O-:3])=[O:2].[NH2:14][CH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>CN(C)C=O>[NH2:13][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][C:7]=1[C:8]([NH:21][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([C:15]#[N:14])=[CH:17][CH:18]=1)=[O:10]

Participants

4

Reactant 2

HCID 120764-Nitroanthranilic acidHCID 826084-(Aminomethyl)benzonitrile

Product 1

HCID 11120008HCID 11120008, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

31.7 g (0.17 mol) of 4-nitro-anthranilic acid are dissolved in 350 ml dimethylformamide and after the addition of 45.4 g (0.28 mol) of N,N′-carbonyldiimidazole stirred for 30 minutes at 50° C. Then a solution of 23 g (0.17 mol) of 4-aminomethyl-benzonitrile in 100 ml dimethylformamide is added dropwise and stirred for 2 hours at 50° C. The solution is evaporated down, dissolved in ethyl acetate and extracted with sodium hydrogen carbonate solution. The combined organic extracts are dried and evaporated down. The residue is chromatographed on silica gel and eluted with methylene chloride/ethanol (97:3).

Workup

  1. stirringstirred for 2 hours at 50° C
  2. customThe solution is evaporated down
  3. dissolutiondissolved in ethyl acetate
  4. extractionextracted with sodium hydrogen carbonate solution
  5. customThe combined organic extracts are dried
  6. customevaporated down
  7. customThe residue is chromatographed on silica gel
  8. washeluted with methylene chloride/ethanol (97:3)

Sources & evidence

ORD record
ord-d3216b848a5d4d0991f5e6a449ef0aab
Source dataset
uspto-grants-2001_03
Patent number
US06200976B1

Reaction notes

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