Acetic Acid → 2-Amino-3-iodo-4-methylbenzoic acid

HRID 2092279Notes

Reaction equation

HRID 2092279 reaction equation
[I:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].C(O)(=O)C.Cl>C(O)C.[Fe]>[NH2:12][C:3]1[C:2]([I:1])=[C:10]([CH3:11])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 529879563-Iodo-4-methyl-2-nitrobenzoic acid

Product 1

HCID 457896112-Amino-3-iodo-4-methylbenzoic acidYield 96.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

3-Iodo-4-methyl-2-nitrobenzoic acid (46.00 g, 150 mmol) was suspended in ethanol (500 mL) and acetic acid (86 mL, 1498 mmol). The mixture was heated to 70° C. and iron (33 g, 599 mmol) was added in small portions. Stirring was continued for 3 h, and then the reaction was cooled down to RT and poured on 1.5 kg of crushed ice and 1 L of 5 N aqueous HCl. The mixture was extracted with ethyl acetate and the organic layer was dried with sodium sulfate, concentrated under vacuum and dried to give 2-amino-3-iodo-4-methylbenzoic acid (40 g, 96%) as a tan solid. MS (M+H)+ 278

Workup

  1. temperaturethe reaction was cooled down to RT
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried with sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customdried

Sources & evidence

ORD record
ord-47a25e384d504983ad19521446e3d516
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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