HCID 178472903, compound → ethyl 6-iodo-4-oxo4H-1,2-benzoxazine-3-carboxylate

HRID 411200Notes

Reaction equation

HRID 411200 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[C:9](=[O:18])[C:10](=[N:16][OH:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C1(C)C=CC=CC=1>[I:8][C:5]1[CH:6]=[CH:7][C:2]2[O:17][N:16]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9](=[O:18])[C:3]=2[CH:4]=1

Participants

3

Reactant 1

HCID 178472903HCID 178472903, compound

Product 1

HCID 22397138ethyl 6-iodo-4-oxo4H-1,2-benzoxazine-3-carboxylateYield 52.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 3-(2-fluoro-5-iodophenyl)-2-(hydroxyimino)-3-oxopropanoate (Preparation 16, 1.3 g) in toluene (20 mL) is heated to reflux under nitrogen for 48 h. The reaction mixture is cooled to room temperature and concentrated in vacuo to give 1.33 g of a crude yellow solid which is recrystallized from ether to afford 0.65 g of the title compound as a yellow crystalline solid. Physical characteristics: mp 130-131: 1H NMR (300 MHz, CDCl3) δ 1.45, 4.51, 7.35, 8.09, 8.50; IR (drift) 2475, 2425, 2382, 2350, 2260, 1742, 1663, 1456, 1332, 1240, 1195, 1150, 1010, 987, 831 cm−1; HRMS (FAB) m/z 345.9581 (C11H8INO4+H). Anal. Found: C, 38.03; H, 2.52; N, 4.06.

Workup

  1. temperatureto reflux under nitrogen for 48 h
  2. concentrationconcentrated in vacuo
  3. customto give 1.33 g of a crude yellow solid which
  4. customis recrystallized from ether

Sources & evidence

ORD record
ord-643ca014295544f68ee9549871045048
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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