HCID 86720217, compound → HCID 86720222, compound

HRID 1754009Notes

Reaction equation

HRID 1754009 reaction equation
[NH2:1][C:2]1[C:17]([CH3:18])=[CH:16][C:15](Br)=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[Cu](C#N)[C:21]#[N:22]>CN1CCCC1=O>[NH2:1][C:2]1[C:17]([CH3:18])=[CH:16][C:15]([C:21]#[N:22])=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

4

Reactant 2

HCID 86720217HCID 86720217, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 86720222HCID 86720222, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The above-described method (Example 2) was repeated to react benzyl 2-amino-5-bromo-3-methylbenzoate (3.00 g, 7.38 mmol) with copper cyanide (0.772 g, 7.98 mmol) in N-methylpyrrolidone at 170° C. for 6 hours. Following working up similar to Example 2, additional extraction with ethyl acetate, washing with aqueous 5% ethylenediamine solution and column chromatography, benzyl 2-amino-5-cyano-3-methylbenzoate (1.00 g, 47.9% of theory, 97.0 area % LC) was obtained as a pale brown solid.

Workup

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

Sources & evidence

ORD record
ord-e87160b613e64a1baaae9d36e2d518ef
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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