Anthranilic Acid → 1,2,3,3a-Tetrahydro-3a-phenyl-5H-pyrrolo[1,2-a]-3,1-benzoxazin-5-one

HRID 249270

Reaction equation

HRID 249270 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[CH2:12][CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[C:17]1([C:15]23[CH2:14][CH2:13][CH2:12][N:1]2[C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4](=[O:6])[O:5]3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 6101p-Toluenesulfonic acidHCID 2535334-Chlorobutyrophenone

Product 1

HCID 197610771,2,3,3a-Tetrahydro-3a-phenyl-5H-pyrrolo[1,2-a]-3,1-benzoxazin-5-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 26.1 g of 2-aminobenzoic acid, 36.5 g of 4-chloro-1-phenyl-1-butanone, 0.5 g of p-toluenesulfonic acid and 250 ml of xylene were refluxed with a water trap. After the reaction was complete, the solvent was removed by distillation and the remaining solid was recrystallized from ethanol. Yield: 41.1 g (81.5%), melting point 152° C.

Workup

  1. temperaturewere refluxed with a water trap
  2. customthe solvent was removed by distillation
  3. customthe remaining solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-db75a1b05ccf4cf8acdc118e9f3e2955
Source dataset
uspto-grants-1993_05
Patent number
US05214047

Linked notes

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