Propionic anhydride → 2-Ethyl-4H-pyrido[2,3-d][1,3]oxazin-4-one

HRID 705110Notes

Reaction equation

HRID 705110 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11](OC(=O)CC)(=O)[CH2:12][CH3:13]>>[CH2:12]([C:13]1[O:5][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[N:10][C:2]=2[N:1]=1)[CH3:11]

Participants

3

Reactant 2

HCID 31263Propionic anhydrideHCID 729302-Aminonicotinic acid

Product 1

HCID 186137472-Ethyl-4H-pyrido[2,3-d][1,3]oxazin-4-oneYield 86%

Conditions

Temperature
120 °C

Procedure

A suspension of 2-aminonicotinic acid (1.0 g 7.24 mmol) in propionic anhydride (10 mL) of was heated to 120° C. for 1 h under nitrogen atmosphere. The temperature was increased to 167° C. to remove the propionic acid and propionic anhydride under reduced pressure. The resulting brown solid was triturated with hexane and dried to give the title pyrido-oxazine (16) (1.10 g, 86%) as a white solid:

Workup

  1. temperatureThe temperature was increased to 167° C.
  2. customto remove the propionic acid and propionic anhydride under reduced pressure
  3. customThe resulting brown solid was triturated with hexane
  4. customdried

Sources & evidence

ORD record
ord-a8760626e5ce49a4819cd5d53a096c70
Source dataset
uspto-grants-2015_11
Patent number
US09173869B2

Reaction notes

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