Anthranilic Acid → 2-(3-Chloro-phenyl)-benzo[d][1,3]oxazin-4-one

HRID 918237Notes

Reaction equation

HRID 918237 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](Cl)=O.O>N1C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([C:15]2[O:9][C:1](=[O:10])[C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[N:4]=2)[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 962WaterHCID 69252Benzoyl chloride, 3-chloro-

Product 1

HCID 7028332-(3-Chloro-phenyl)-benzo[d][1,3]oxazin-4-oneYield 96.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 76.5 g (0.56 mole) of anthranilic acid in 1000 ml of pyridine at room temperature was added 197 g (1.12 mole) of m-chlorobenzoyl chloride at a rapid dropwise rate. The temperature rose to 45°-50° and, midway through the addition, a precipitate began forming. After stirring one hour at room temperature the slurry was poured into 1500 ml of water and the precipitate was filtered, washed well with water and air dried to give 139 g (96.5%) of 2-(m-chlorophenyl)-4H-3,1-benzoxazin-4-one, m.p. 158°-60°. Crystallization from ethanol gave an analytical sample, m.p. 159°-60°.

Workup

  1. additionThe temperature rose to 45°-50° and, midway through the addition
  2. customa precipitate began forming
  3. filtrationthe precipitate was filtered
  4. washwashed well with water and air
  5. customdried

Sources & evidence

ORD record
ord-70dab278861f477e8f514145282a9dea
Source dataset
uspto-grants-1976_07
Patent number
US03970652

Reaction notes

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