Hydrogen Peroxide → HCID 10039448, compound

HRID 375610Notes

Reaction equation

HRID 375610 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5](=[C:9]([Cl:11])[CH:10]=1)[C:6]([OH:8])=O.[NH:13]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)C(=O)C1=O.OO.ClC1C=CC=C(C(O)=O)C=1N.NOC1CCCCCC=1>C1(C)C=CC=CC=1>[Cl:11][C:9]1[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]2[C:5]=1[C:6](=[O:8])[N:13]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:23]1=[N:12]2

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 7054IsatinHCID 808072-Amino-3-chlorobenzoic acidHCID 2904984,6-Dichloroanthranilic acidHCID 18353297HCID 18353297, compound

Product 1

HCID 10039448HCID 10039448, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of 15 g of 4,6-dichloroanthranilic acid (prepared from the corresponding isatine: T. Sandmeyer Helv. Chim. Acta, 2:234 (1919), by oxidation with alkaline hydrogen peroxide, following the procedure described by Baker et al., J. Org. Chem., 17:141 (1952) for the synthesis of 3-chloroanthranilic acid) in 100 mL of toluene was added 20 g of 1-aza-2-methoxy-1-cycloheptene. The mixture was stirred for an hour at room temperature, followed by heating under reflux for 18 hours. Then the mixture was concentrated in vacuo and volatile material was removed at 130° C. at 1 torr. The dark brown residue was chromatographed using 8:1 chloroform-ethyl acetate to give 9 g of the desired material as a crystalline solid, m.p. 110° C.-112° C.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 18 hours
  3. concentrationThen the mixture was concentrated in vacuo and volatile material
  4. customwas removed at 130° C. at 1 torr
  5. customThe dark brown residue was chromatographed

Sources & evidence

ORD record
ord-ef68880949b14d9a9fc2e31645dd8e5c
Source dataset
uspto-grants-1996_01
Patent number
US05486512

Reaction notes

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