Salicylamide → 2-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

HRID 1620893Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])N(C2C=CC(C(O)=O)=CC=2)N=1.C(N)(=O)C1C(=CC=CC=1)[OH:32].C(Cl)(=O)C1C(=CC=CC=1)O>>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:11](=[O:32])[N:12]=1

Participants

Reactant 3

HCID 5147Salicylamide

HCID 74041Salicyloyl chloride

HCID 214348Deferasirox

Product 1

HCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Conditions

Temperature: 170 °C

Procedure

U.S. Pat. No. 6,465,504 discloses substituted 3,5-diphenyl-1,2,4-triazoles and their use as pharmaceutical metal chelators. This patent describes a process for the preparation of 4-[3,5-Bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid (deferasirox) (1) that involves the condensation of salicylamide (2) with salicyloyl chloride (3) by heating at 170° C. yielding 2-(2-hydroxyphenyl)-benz[e][1,3]oxazin-4-one (5), which reacts with 4-hydrazinobenzoic acid (6) in refluxing ethanol to give (1) (Scheme 1):

Sources & evidence

ORD record: ord-e6a44cd9d68a40d58462d96d3444abde
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772503B2

Reaction notes

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