Nitric Acid → 3-(Formylamino)-6-bromo-4-methyl-2-nitrobenzoic Acid

HRID 968802Notes

Reaction equation

HRID 968802 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]([NH:7][C:8]1[CH:9]=[C:10]([C:14]([Br:18])=[CH:15][C:16]=1[CH3:17])[C:11]([OH:13])=[O:12])=[O:6]>>[CH:5]([NH:7][C:8]1[C:9]([N+:1]([O-:4])=[O:2])=[C:10]([C:14]([Br:18])=[CH:15][C:16]=1[CH3:17])[C:11]([OH:13])=[O:12])=[O:6]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 590163162-Bromo-5-(formylamino)-4-methylbenzoic acid

Product 1

HCID 590163123-(Formylamino)-6-bromo-4-methyl-2-nitrobenzoic Acid

Conditions

Temperature
0 °C

Procedure

Fuming nitric acid (120 mL, 2.8 mol) is cooled to about 0° C., whereupon 3-(Formylamino)-6-bromo-4-methylbenzoic Acid (20) (28.243 g, 109.5 mmol) is added in small portions over about 45 minutes, at such a rate to maintain the internal reaction temperature <5° C. The reaction mixture is then stirred at about 0° C. for about 1 hour. The reaction mixture is added to ice water (500 mL) and stirred for about 1 hour. The solids that form are filtered and dried to provide 3-(Formylamino)-6-bromo-4-methyl-2-nitrobenzoic Acid (21), as a beige powder (31.465 g, 95% yield).

Workup

  1. additionis added in small portions over about 45 minutes
  2. temperatureat such a rate to maintain the internal reaction temperature <5° C
  3. stirringstirred for about 1 hour
  4. filtrationThe solids that form are filtered
  5. customdried

Sources & evidence

ORD record
ord-56eb73e4863e46d99b413ab101a12527
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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