Acetic Anhydride → HCID 52919049, compound

HRID 2175684Notes

Reaction equation

HRID 2175684 reaction equation
[OH:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]/[C:12]([NH:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:24](OC(=O)C)(=[O:26])[CH3:25]>O>[C:24]([O:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])/[CH:10]=[CH:11]/[C:12]1[O:19][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[N:14]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10018452HCID 10018452, compound

Product 1

HCID 52919049HCID 52919049, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (E)-2-[[3-(3-hydroxy-4-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 it for 1 h and the precipitate was collected by filtration, providing (E)-2-(3-acetoxy-4-methoxystyryl)-4H-benzo[d][1,3]oxazin-4-one (0.50 g, 93%) as a yellow solid; mp 187-190° C.; δH (400 MHz, DMSO-d6) 2.80 (s, 3H, COCH3), 3.83 (s, 3H, OCH3), 6.87 (d, J=16.0 Hz, 1H, CH═CHCO), 7.19 (d, J5′,6=8.0 Hz, 1H, H5′), 7.68 (d, J5′,6=8.0, 1H, H6′), 7.57 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.60 (d, J3,4=8.0 Hz, 1H, H3), 7.66 (s, 1H, H2′), 7.71 (d, J=16.0 Hz, 1H, CH═CHCO), 7.89 (t, J4,5=J5,6=8.0 Hz, 1H, H5), 8.10 (d, J5,6=8.0 Hz, 1H, H6); δC (100 MHz, DMSO-d6) 20.4, 56.1, 112.9, 116.7, 117.6, 122.1, 127.5, 128.0, 128.1, 128.2, 136.8, 139.6, 140.2, 146.7, 152.7, 157.0, 158.8, 168.4; HRMS (ESI) calculated for C19H15NO5 [M+H]+ 338.1023, found 338.1023; νmax 1197, 1268, 1588, 1631, 1752 cm−1.

Workup

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

Sources & evidence

ORD record
ord-606c157309ab45e0a5babb9ce63ad45f
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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