Nitric Acid → HCID 19977470, compound

HRID 1451110Notes

Reaction equation

HRID 1451110 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]([O:8][CH3:9])=[O:7])=[O:2].[N+:18]([O-])([OH:20])=[O:19]>O>[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:18]([O-:20])=[O:19])[C:12]=1[NH:13][S:14]([CH3:17])(=[O:15])=[O:16])[C:6]([O:8][CH3:9])=[O:7])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10825027HCID 10825027, compound

Product 1

HCID 19977470HCID 19977470, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 3-formyl-4-[(methylsulfonyl)amino]benzoate (3.85 g, 0.015 mol) was added portionwise to fuming nitric acid (45 mL) at 5°-10° C. over 0.25 h. The mixture was further stirred for 1.0 h at room temperature and then poured into cold water (200 mL). The yellow precipitate was collected by filtration and washed several times with cold water. The cake was recrystallized from ethyl acetate-hexane to give 2.5 g (55.3%) of methyl 3-formyl-4-[(methylsulfonyl)amino]-5-nitrobenzoate as light yellow needles, mp 158°-160° C.

Workup

  1. filtrationThe yellow precipitate was collected by filtration
  2. washwashed several times with cold water
  3. customThe cake was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-685e9dbf52224797902b1dc796540c5e
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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