Azobisisobutyronitrile → 3-(dimethylphosphinyl)-propyl N-(7-chloro-4-quinolyl)-anthranilate

HRID 971620

Reaction equation

HRID 971620 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[C:14](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:25][PH:26](=[O:28])[CH3:27].N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[C:14](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:15]([O:17][CH2:18][CH2:19][CH2:20][P:26]([CH3:27])([CH3:25])=[O:28])=[O:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 12669156HCID 12669156, compoundHCID 178503022methylphosphonoylmethane2×

Product 1

HCID 126691533-(dimethylphosphinyl)-propyl N-(7-chloro-4-quinolyl)-anthranilate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 3.37 grams (0.01 mol) of allyl 7-chloro-4-quinolyl-anthranilate (melting point 112° C.) dissolved in 60 ml of toluene and 1.17 grams (0.015 mol) of dimethylphosphine oxide is heated to 100° C. 30 mg of α,α'-azo-bis-isobutyronitrile in 10 ml of toluene are then added dropwise to catalyse the addition of the dimethylphosphine oxide to the allyl double bond. From the cooled solution, 3-(dimethylphosphinyl)-propyl N-(7-chloro-4-quinolyl)-anthranilate is isolated; melting point 162° C. (after recrystallisation from acetone); yield: 3.58 grams (86% of theory).

Sources & evidence

ORD record
ord-c2425d3a5ae74127a047f4b61bb360fb
Source dataset
uspto-grants-1979_07
Patent number
US04160828

Linked notes

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