1-Butanol → Butyl anthranilate

HRID 1105941Notes

Reaction equation

HRID 1105941 reaction equation
[H-].[Na+].[NH:3]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])C1=O.[CH2:14](O)[CH2:15][CH2:16][CH3:17].[OH:19]O>CN(C)C=O>[C:6]([O:7][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:19])[C:8]1[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:3]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 784Hydrogen PeroxideHCID 7054IsatinHCID 24758Sodium hydride

Product 1

HCID 24433Butyl anthranilateYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.6 parts of 50 percent strength by weight sodium hydride are added to 14.7 parts of isatin in 250 parts of n-butanol and 100 parts of dimethylformamide at 25° C. After one hour, 8 parts of 50 percent strength by weight hydrogen peroxide solution are slowly added to the violet solution, and the temperature is allowed to rise to 50° C. The mixture is then stirred for one hour and is worked up as described in Example 1. 10.8 parts (56% of theory) of n-butyl anthranilate are obtained.

Workup

  1. customto rise to 50° C

Sources & evidence

ORD record
ord-e3e0c1a158da47a4af6efb62bb9db462
Source dataset
uspto-grants-1982_01
Patent number
US04310677

Reaction notes

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