Methyl Anthranilate → Methyl 2-amino-5-iodobenzoate hydrochloride

HRID 1276614Notes

Reaction equation

HRID 1276614 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I:12][Cl:13]>C(O)(=O)C>[ClH:13].[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 8635Methyl AnthranilateHCID 24640Iodine chloride

Product 1

HCID 22116523Methyl 2-amino-5-iodobenzoate hydrochlorideYield 83.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 25 g (0.165 mol) of methyl 2-aminobenzoate in 3 L of glacial acetic acid was added a second solution of 26.82 g (0.165 mol)iodine monochloride in 250 mL of glacial acetic acid over 20-30 min. The resulting mixture was stirred at room temperature for 24 h. The ensuing precipitate was filtered, washed with glacial acetic acid followed by diethyl ether, and dried to provide 43.2 g of the title compound, which was generally used without further purification in subsequent steps, m.p. 188-192° C.; 1H NMR (300 MHz, Me2SO--d6): δ3.79 (s,3H); 6.67 (d,1H); 7.50 (dd,1H); 7.93 (d,1H). Anal. Calcd. for C8H9NO2ICl: C, 30.65; H, 2.89; N, 4.47; O, 10.21; Cl, 11.31; I, 40.48. Found: C, 31.19; H, 2.85; N, 4.48; 0, 10.27; Cl, 11.72; I, 40.15.

Workup

  1. filtrationThe ensuing precipitate was filtered
  2. washwashed with glacial acetic acid
  3. customdried

Sources & evidence

ORD record
ord-5407aef3c4d247b1ac3e136a8e1a9f10
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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