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

HRID 1358506Notes

Reaction equation

HRID 1358506 reaction equation
[C:1](Cl)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:11]([NH2:20])(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)O.Cl>>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]1[O:9][C:18]2[CH:17]=[CH:16][CH:15]=[CH:13][C:12]=2[C:11](=[O:19])[N:20]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 5147SalicylamideHCID 74041Salicyloyl chloride

Product 1

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

Procedure

106.0 g of salicyloyl chloride and 93.0 g of salicylamide are mixed and heated at 170° C. for 30 min until hydrogen chloride no longer escapes. The mixture is cooled and the residue is crystallized from ethanol. After drying, 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one is obtained as slightly yellow crystals of m.p. 206-208° C.

Workup

  1. temperatureThe mixture is cooled
  2. customthe residue is crystallized from ethanol
  3. customAfter drying

Sources & evidence

ORD record
ord-b303e273ae9745e0aab89ba29443aaf0
Source dataset
uspto-grants-2003_07
Patent number
US06596750B2

Reaction notes

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