Acetic Anhydride → HCID 12210169, compound

HRID 1771965Notes

Reaction equation

HRID 1771965 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](OC(=O)C)(=O)[CH3:14]>>[CH3:12][O:11][C:10]1[C:2]2[N:1]=[C:13]([CH3:14])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 12210169HCID 12210169, compoundYield 100%

Conditions

Temperature
140 °C

Procedure

To a 100 mL round-bottomed flask, 2-amino-3-methoxybenzoic acid (10.1 g, 60.4 mmol) and acetic anhydride (50 ml, 530 mmol) were added to give a suspension. The mixture was heated to 140° C. with stirring for 180 min. The reaction mixture was cooled to room temperature and concentrated to provide 8-methoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one (11.51 g, 100%): 1H NMR (400 MHz, DMSO-d6) δ 7.59 (dd, J=6.9, 2.3 Hz, 1H), 7.52-7.42 (m, 2H), 3.89 (s, 3H), 2.39 (s, 3H); HPLC: RT=0.795 min (H2O/MeOH with TFA, Sunfire C18 2.5 μm, 2.1×30 mm, gradient=2 min, wavelength=220 nm); MS(ES): m/z=292 [M+H]+.

Workup

  1. customto give a suspension
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9a2006e4086f46608dfcb4ca38a1bc3e
Source dataset
uspto-grants-2016_02
Patent number
US09249157B2

Reaction notes

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