Acetic Anhydride → HCID 52918810, compound

HRID 2175682Notes

Reaction equation

HRID 2175682 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=O)=[CH:4][C:3]=1[O:22][CH3:23].[C:24](OC(=O)C)(=[O:26])[CH3:25]>O>[C:24]([O:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[O:17][C:15](=[O:16])[C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[N:12]=2)=[CH:4][C:3]=1[O:22][CH3:23])(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10245047Avenanthramide E

Product 1

HCID 52918810HCID 52918810, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (E)-2-[[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.5 g, 1.6 mmol) in acetic anhydride (3 mL) was heated to reflux and stirred for 3 h. The reaction was cooled to rt and the resulting suspension was diluted with water. The suspension was stirred at rt for 1 h and the precipitate was collected by filtration, providing (E)-2-(4-acetoxy-3-methoxystyryl)-4H-benzo[d][1,3]oxazin-4-one (0.52 g, 97%) as a pale brown solid; mp 185-186° C.; δH (400 MHz, DMSO-d6) 2.63 (s, 3H, COCH3), 3.85 (s, 3H, OCH3), 7.08 (d, J=16.0 Hz, 1H, CH═CHCO), 7.17 (d, J5′,6′=8.0 Hz, 1H, H5′), 7.38 (d, J5′,6′=8.0, 1H, H6′), 7.59 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.61 (d, J3,4=8.0 Hz, 1H, H3), 7.63 (s, 1H, H2′), 7.76 (d, J=16.0 Hz, 1H, CH═CHCO), 7.92 (t, J4,5=J5,6=8.0 Hz, 1H, H5), 8.11 (d, J5,6=8.0 Hz, 1H, H6); δC (100 MHz, DMSO-d6) 20.4, 56.0, 111.9, 116.9, 119.5, 121.4, 123.3, 126.6, 128.1, 128.4, 133.5, 136.8, 140.5, 140.9, 146.6, 151.2, 156.8, 168.4; HRMS (ESI) calculated for C19H5NO5 [M+H]+ 338.1023; found 338.1023; νmax 1197, 1214, 1593, 1635, 1748 cm−1.

Workup

  1. temperatureto reflux
  2. stirringThe suspension was stirred at rt for 1 h
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8ef42e38cbf24c53a97077c59c8e9fb4
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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