HCID 86720216, compound → HCID 86720221, compound

HRID 1754008Notes

Reaction equation

HRID 1754008 reaction equation
[NH2:1][C:2]1[C:14]([CH3:15])=[CH:13][C:12](Br)=[CH:11][C:3]=1[C:4]([O:6][CH2:7][CH2:8][O:9][CH3:10])=[O:5].[Cu](C#N)[C:18]#[N:19]>CN1CCCC1=O>[NH2:1][C:2]1[C:14]([CH3:15])=[CH:13][C:12]([C:18]#[N:19])=[CH:11][C:3]=1[C:4]([O:6][CH2:7][CH2:8][O:9][CH3:10])=[O:5]

Participants

4

Reactant 2

HCID 86720216HCID 86720216, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 86720221HCID 86720221, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The above-described method (Example 2) was repeated to react 2-methoxyethyl 2-amino-5-bromo-3-methylbenzoate (5.00 g, 15.88 mmol) with copper cyanide (1.49 g, 16.67 mmol) in N-methylpyrrolidone 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, 2-methoxyethyl 2-amino-5-cyano-3-methylbenzoate (0.45 g, 11.6% of theory, 95.6 area % LC) was obtained as a brown solid.

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-5a1775fb45994b28a1f7fcc8b1f1b354
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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