Isatoic Anhydride → 2-(3-Methyl-1,2,4-oxadiazol-5-yl)aniline

HRID 1041753Notes

Reaction equation

HRID 1041753 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])OC1=O.O[NH:14][C:15](=[NH:17])[CH3:16].CCN(C(C)C)C(C)C>C1COCC1>[CH3:16][C:15]1[N:17]=[C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH2:1])[O:11][N:14]=1

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 81531DiisopropylethylamineHCID 178465666HCID 178465666, compound

Product 1

HCID 126766822-(3-Methyl-1,2,4-oxadiazol-5-yl)anilineYield 69.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1H-benzo[d][1,3]oxazine-2,4-dione (3.5 g) in THF (35 mL) was treated with N-hydroxy-acetamidine (1.7 g), and DIEA (8 mL). The reaction mixture was microwave heated at 180° C. for 5 minutes, concentrated and purified by silica gel chromatography to afford 2.6 g of 2-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenylamine: 1H NMR (300 MHz, CDCl3) δ 8.0 (d, 1H), 7.4 (t, 1H), 6.9 (m, 2H), 6.0 (bs, 2H), 2.6 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-2f34ff2bc1be4b27937219729507e98f
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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