Anthranilic Acid → 2-(1-Chloroethyl)-4H-3,1-benzoxazin-4-one

HRID 1153800Notes

Reaction equation

HRID 1153800 reaction equation
[Cl:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11]>C1(C)C=CC=CC=1>[Cl:1][CH:2]([C:3]1[O:4][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[N:7]=1)[CH3:6]

Participants

4

Reactant 2

HCID 227Anthranilic AcidHCID 1110192-Chloropropionyl chloride

Product 1

HCID 134230792-(1-Chloroethyl)-4H-3,1-benzoxazin-4-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

17.47 ml of 2-chloropropionic acid chloride were added with stirring at room temperature to a solution of 10.3 g of 2-amino-benzoic acid in 20 ml of toluene and the mixture was progressively heated to 65° C. during which a mass was formed and gas disengaged and the mixture fluidized. The mixture was held at reflux for 90 minutes and was evaporated to dryness under reduced pressure. The residue was empasted with petroleum ether (b.p.=60° to 80° C.), was iced and vacuum filtered. The product was washed and dried under reduced pressure at 50° C. to obtain 14.45 g of 2-(1-chloroethyl)-4H-3,1-benzoxazine-4-one melting at 90° C.

Workup

  1. customwas formed
  2. temperatureat reflux for 90 minutes
  3. customwas evaporated to dryness under reduced pressure
  4. filtrationvacuum filtered
  5. washThe product was washed
  6. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-cdc73cbdddbf4794803f53dd957de75c
Source dataset
uspto-grants-1984_12
Patent number
US04486438

Reaction notes

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