Ethyl 2-amino-3-(hydroxy(oxido)amino)benzoate → HCID 18355136, compound

HRID 429669Notes

Reaction equation

HRID 429669 reaction equation
[N+:1]([C:4]1[C:5]([NH2:15])=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-:3])=[O:2].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>CN(C)C1C=CC=CC=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[N+:1]([C:4]1[C:5]([NH:15][C:16]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[O:23])=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 393670Ethyl 2-amino-3-(hydroxy(oxido)amino)benzoateHCID 417436Pyridine-4-carbonyl chloride

Product 1

HCID 18355136HCID 18355136, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 949N,N-DimethylanilineSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of ethyl 3-nitro-2-aminobenzoate (700 mg) in N,N-dimethylaniline (7 ml) was added dropwise isonicotinoyl chloride (2.96 g) at 120° C. for 3 hours. After cooling, the reaction mixture was diluted with ethyl acetate and saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and washed with brine. The solution was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1) to give ethyl 3-nitro-2-(4-pyridyl)carbonylaminobenzoate (200 mg).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-e0c57ce788b44cb78d77ba7eb8c69f36
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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