HCID 86720214, compound → HCID 86720219, compound

HRID 1754005Notes

Reaction equation

HRID 1754005 reaction equation
[NH2:1][C:2]1[C:16]([CH3:17])=[CH:15][C:14](Br)=[CH:13][C:3]=1[C:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:5].[Cu](C#N)[C:20]#[N:21]>CN(C)C(=O)C>[NH2:1][C:2]1[C:16]([CH3:17])=[CH:15][C:14]([C:20]#[N:21])=[CH:13][C:3]=1[C:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 86720214HCID 86720214, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 86720219HCID 86720219, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The above-described method (Example 2) was repeated to react hexyl 2-amino-5-bromo-3-methylbenzoate (2.2 g, 6.79 mmol) with copper cyanide (0.62 g, 6.93 mmol) in N,N-dimethylacetamide at 170° C. for 6 hours. Following working up similar to Example 2 and additional extraction with ethyl acetate and washing with aqueous 5% ethylenediamine solution, hexyl 2-amino-5-cyano-3-methylbenzoate (1.66 g, 85.5% of theory, 91.1 area % LC) was obtained as a brown oil.

Workup

  1. extractionFollowing working up similar to Example 2 and additional extraction with ethyl acetate
  2. washwashing with aqueous 5% ethylenediamine solution

Sources & evidence

ORD record
ord-77796cadd11c4da683302ff610f06848
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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