HCID 54593425, compound → HCID 25156989, compound

HRID 1754007Notes

Reaction equation

HRID 1754007 reaction equation
[NH2:1][C:2]1[C:12]([CH3:13])=[CH:11][C:10](Br)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cu](C#N)[C:16]#[N:17]>CN(C)C(=O)C>[NH2:1][C:2]1[C:12]([CH3:13])=[CH:11][C:10]([C:16]#[N:17])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 54593425HCID 54593425, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 25156989HCID 25156989, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The above-described method (Example 2) was repeated to react ethyl 2-amino-5-bromo-3-methylbenzoate (2.00 g, 7.65 mmol) with copper cyanide (0.70 g, 7.80 mmol) in N,N-dimethylacetamide at 160° C. for 8 hours. Following working up similar to Example 2, ethyl 2-amino-5-cyano-3-methylbenzoate (1.30 g, 80.2% of theory, 96.3 area % LC) was obtained as a brown solid.

Sources & evidence

ORD record
ord-49baf5ececd54d2697adf98b7b9ffd0d
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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