Nitric Acid → HCID 22485016, compound

HRID 2181051Notes

Reaction equation

HRID 2181051 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[C:5]([NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([Cl:19])[CH:10]=1)(=[O:7])[CH3:6]>O>[C:5]([NH:8][C:9]1[C:18]([N+:1]([O-:4])=[O:2])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([Cl:19])[CH:10]=1)(=[O:7])[CH3:6].[C:5]([NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([Cl:19])[C:10]=1[N+:1]([O-:3])=[O:2])(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 15055536HCID 15055536, compound

Product 2

HCID 13912863HCID 13912863, compoundHCID 22485016HCID 22485016, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Fuming nitric acid (26 ml) was cooled to −35° C. and stirred. Methyl 4-acetamido-2-chlorobenzoate (6.5 g) was added at from −35° C. to −25° C., and the mixture was stirred for 3 hr. The reaction mixture was ice-cooled and H2O (260 ml) was poured therein, which was followed by stirring. The resulting crystals were collected by filtration, washed with water and dried with air. This was applied to flash silica gel column chromatography (silica gel 100 g) to give methyl 4-acetamido-2-chloro-5-nitrobenzoate as thin yellow crystals (5.32 g) and methyl 4-acetamido-2-chloro-3-nitrobenzoate as a yellow solid (ca. 1.7 g, 22% yield).

Workup

  1. stirringthe mixture was stirred for 3 hr
  2. temperaturecooled
  3. stirringby stirring
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with water
  6. customdried with air

Sources & evidence

ORD record
ord-0335afe0450e4214a0174fc07ec4fa7c
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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