Isatoic Anhydride → HCID 59375063, compound

HRID 1811013Notes

Reaction equation

HRID 1811013 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=O)[O:3][C:2]1=O.[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].COC(OC)OC>C1COCC1>[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([N:17]2[C:4](=[O:3])[C:5]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:1]=[CH:2]2)[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 9005Trimethyl orthoformateHCID 1235383-Bromo-o-toluidine

Product 1

HCID 59375063HCID 59375063, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1H-benzo[d][1,3]oxazine-2,4-dione (200 mg, 1.226 mmol), 3-bromo-2-methylaniline (228 mg, 1.226 mmol), and trimethoxymethane (390 mg, 3.68 mmol) in THF (2 mL) was heated overnight in a sealed tube at 100° C. The mixture was cooled to rt and concentrated, and the residue was purified by column chromatography (eluting with 90:10 to 50:50 hexane-EtOAc) to give 3-(3-bromo-2-methylphenyl)quinazolin-4(3H)-one (140 mg, 36%). 1H NMR (400 MHz, chloroform-d) δ 8.37 (1 H, dd, J=8.3, 1.2 Hz), 7.97 (1 H, s), 7.76-7.86 (2 H, m), 7.72 (1 H, t, J=4.6 Hz), 7.57 (1 H, ddd, J=8.0, 6.7, 1.5 Hz), 7.21-7.28 (2 H, m), 2.26 (3 H, s). Mass spectrum m/z 315, 317 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated
  3. customthe residue was purified by column chromatography (eluting with 90:10 to 50:50 hexane-EtOAc)

Sources & evidence

ORD record
ord-30735fbbf8154dc9b3f625343ba1220b
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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