Formic Acid → 2-Bromo-5-(formylamino)-4-methylbenzoic acid

HRID 968801Notes

Reaction equation

HRID 968801 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([Br:12])=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[CH:13](O)=[O:14]>>[CH:13]([NH:1][C:2]1[CH:3]=[C:4]([C:8]([Br:12])=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6])=[O:14]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 533302755-Amino-2-bromo-4-methylbenzoic acid

Product 1

HCID 590163162-Bromo-5-(formylamino)-4-methylbenzoic acid

Procedure

A mixture of 3-Amino-6-bromo-4-methylbenzoic Acid (19) (6.4145 g, 27.88 mmol) in 90% aqueous formic acid (36 mL) is heated to reflux for about 3 hours. The mixture is then cooled to ambient temperature, added to ice water (150 mL) and stirred for about 15 minutes. The solids that form are filtered and dried to provide 3-(Formylamino)-6-bromo-4-methylbenzoic Acid (20):, as a purple-pink solid (5.961 g, 82% Yield).

Workup

  1. temperatureis heated
  2. temperatureto reflux for about 3 hours
  3. filtrationThe solids that form are filtered
  4. customdried

Sources & evidence

ORD record
ord-c00ca5fde1df427082e5f0f761f27346
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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