Water → Isophthalamic acid

HRID 1726759Notes

Reaction equation

HRID 1726759 reaction equation
IC1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](N)=[O:6].[OH2:11].C([N:14]([CH2:17][CH3:18])CC)C.C1(P(C(P(C2C=CC=CC=2)C2C=CC=CC=2)(C)C)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:49]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:5]([C:4]1[CH:3]=[C:18]([CH:10]=[CH:9][CH:8]=1)[C:17]([NH2:14])=[O:49])([OH:11])=[O:6]

Participants

8

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 2024253-IodobenzamideHCID 12091099Phosphine, (1-methylethylidene)bis[diphenyl-HCID 178418416HCID 178418416, compound

Product 1

HCID 3014284Isophthalamic acidYield 87%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-iodobenzamide (4.28 g, 17.3 mmol), water (25.00 g, 1387.7 mmol), triethylamine (8.00 g, 79.1 mmol), palladium(II) acetate (0.28 g, 1.2 mmol), and bis(diphenylphosphino)propane (0.52 g, 1.3 mmol) in acetonitrile (50 mL) was pressurized to 40 psi with carbon monoxide and the pressure was released. After six such cycles, the bottle was pressurized again and the contents were stirred at 85° C. for 3 h. The reaction mixture was cooled to room temperature and depressurized. The solvent was evaporated and ethyl acetate (200 mL) was added. The solution was filtered and then extracted with water (2×200 mL). The combined aqueous layers were acidified with 12 M HCl to pH 0. The solid was filtered off and air-dried to give 3-carboxybenzamide (1.93 g, 87%) as a yellow solid

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solvent was evaporated
  3. additionethyl acetate (200 mL) was added
  4. filtrationThe solution was filtered
  5. extractionextracted with water (2×200 mL)
  6. filtrationThe solid was filtered off
  7. customair-dried

Sources & evidence

ORD record
ord-05f01c1c750f4cb99bd20f2ddcd16376
Source dataset
uspto-grants-2009_02
Patent number
US07491741B2

Reaction notes

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