Acetic Anhydride → 5-Azaacetanthranil

HRID 1097548Notes

Reaction equation

HRID 1097548 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:11](OC(=O)C)(=O)[CH3:12]>>[CH3:11][C:12]1[O:9][C:8](=[O:10])[C:3]2[N:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 738363-Aminopicolinic acid

Product 1

HCID 122042175-Azaacetanthranil

Procedure

Imidazo[4,5-c][1,5]naphthyridine-2,4-diamines of the invention can be prepared according to Reaction Scheme V, wherein D, R, R1, R4a, Ph, m, and p are as defined above. 3-Aminopyridine-2-carboxylic acids of Formula XXXIII are known and can be prepared by known methods. The compound where n and m are both 0 is commercially available. In step (1) of Reaction Scheme V, a 3-aminopyridine-2-carboxylic acid of Formula III is heated with acetic anhydride to provide a 2-methyl-4H-pyrido[3,2-d][1,3]oxazin-4-one of Formula XXXIV.

Workup

  1. customaccording to Reaction Scheme V, wherein D, R, R1, R4a, Ph, m, and p
  2. customcan be prepared
  3. customIn step (1) of Reaction Scheme V

Sources & evidence

ORD record
ord-9b3b22b2ecd04bc9b4df3ec658b5d902
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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