Water → 3-Chloro-4-cyano-2-methylphenylacetamide

HRID 501563

Reaction equation

HRID 501563 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[C:4]([CH3:12])[C:3]=1[Cl:13].[Cu](C#N)[C:15]#[N:16].O>CN(C=O)C>[Cl:13][C:3]1[C:4]([CH3:12])=[C:5]([CH2:8][C:9]([NH2:11])=[O:10])[CH:6]=[CH:7][C:2]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 962WaterHCID 684571414-Bromo-3-chloro-2-methylphenylacetamideHCID 178418260HCID 178418260, compound

Product 1

HCID 684580283-Chloro-4-cyano-2-methylphenylacetamideYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of bromide 23B (2.70 g, 10.3 mmol) and copper cyanide (0.92 g, 10.3 mmol) in DMF (30 mL) was heated to 150° C. for 4 h. The suspension was cooled, poured into water with stirring, and the solid was filtered and dried to give 1.44 g (67%) of the desired nitrile. 1H NMR (DMSO-d6) δ 2.12 (s, 3H), 2.29 (s, 3H), 7.72 (d, J=8.8, 1H), 7.75 (d, J=8.2, 1H), 9.73 (s, 1H); 13C NMR (DMSO-d6) δ 15.3, 23.5, 107.7, 116.5, 123.0, 130.1, 131.5, 135.7, 142.3, 168.8; HPLC a) column: Phenomenex ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.23 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.13 min retention time (95%); MS (ES) m/z 209 [M+H]+.

Workup

  1. temperatureThe suspension was cooled
  2. filtrationthe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-d844cb90b5d14c16995b04122b46d392
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Linked notes

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