HCID 86720215, compound → HCID 86720220, compound

HRID 1754006Notes

Reaction equation

HRID 1754006 reaction equation
[NH2:1][C:2]1[C:18]([CH3:19])=[CH:17][C:16](Br)=[CH:15][C:3]=1[C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5].[Cu](C#N)[C:22]#[N:23]>CN(C)C(=O)C>[NH2:1][C:2]1[C:18]([CH3:19])=[CH:17][C:16]([C:22]#[N:23])=[CH:15][C:3]=1[C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 86720215HCID 86720215, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 86720220HCID 86720220, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The above-described method (Example 2) was repeated to react 2-ethylhexyl 2-amino-5-bromo-3-methylbenzoate (2.00 g, 5.84 mmol) with copper cyanide (0.53 g, 5.96 mmol) in N,N-dimethylacetamide at 160° C. for 8 hours. Following working up similar to Example 2 and additional washing with aqueous 5% ethylenediamine solution, 2-ethylhexyl 2-amino-5-cyano-3-methylbenzoate (1.45 g, 76.7% of theory, 89.1 area % LC) was obtained as a brown oil.

Workup

  1. washadditional washing with aqueous 5% ethylenediamine solution

Sources & evidence

ORD record
ord-a2e55c97873a41639e54698a0ab94bb4
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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