HCID 86720213, compound → HCID 86720218, compound

HRID 1754004Notes

Reaction equation

HRID 1754004 reaction equation
[NH2:1][C:2]1[C:15]([CH3:16])=[CH:14][C:13](Br)=[CH:12][C:3]=1[C:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:5].[Cu](C#N)[C:19]#[N:20]>CN(C)C(=O)C>[NH2:1][C:2]1[C:15]([CH3:16])=[CH:14][C:13]([C:19]#[N:20])=[CH:12][C:3]=1[C:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:5]

Participants

4

Reactant 2

HCID 86720213HCID 86720213, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 86720218HCID 86720218, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The above-described method (Example 2) was repeated to react pentyl 2-amino-5-bromo-3-methylbenzoate (2.3 g, 7.59 mmol) with copper cyanide (0.69 g, 7.74 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, pentyl 2-amino-5-cyano-3-methylbenzoate (1.78 g, 89.2% of theory, 93.6 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-5fdcef5cc01847018627680600c23eaa
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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