5-Iodosalicylic acid → N-cyclopropyl-2-hydroxy-5-iodo-benzamide

HRID 963419Notes

Reaction equation

HRID 963419 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH:12]1([NH:15][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([I:11])[CH:9]=[CH:10][C:2]=2[OH:1])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 83885-Iodosalicylic acidHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69828Cyclopropylamine

Product 1

HCID 19081760N-cyclopropyl-2-hydroxy-5-iodo-benzamideYield 18.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13bh) A mixture of 2.64 g of 2-hydroxy-5-iodo-benzoic acid, 0.69 g of cyclopropylamine and 3.65 g of carbon tetrabromide in 40 ml of methylene chloride is treated portionwise at room temperature with 2.62 g of triphenylphosphine. After 2 hrs. the mixture is filtered and the filtrate is concentrated. Chromatography on silica gel with ethyl acetate/cyclohexane 1:4 gives 550 mg of crude N-cyclopropyl-2-hydroxy-5-iodo-benzamide. Yield: 18%.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-306d3aab035e4e08a8f3d9d6b64efce8
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

Loading…