HCID 66813086, compound → HCID 66813041, compound

HRID 333764Notes

Reaction equation

HRID 333764 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH:10]([C:13]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=1)=[O:14])C#N>Br>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:10][C:13]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=1)=[O:14]

Participants

3

Reactant 1

HCID 66813086HCID 66813086, compound

Product 1

HCID 66813041HCID 66813041, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2-(2-Chloro-4-methoxy-phenyl)-3-(2-methyl-pyridin-4-yl)-3-oxo-propionitrile (1.2 g, 4.0 mmol) was suspended in aqueous HBr (48%, 12 mL) and heated to reflux overnight. Upon cooling, the precipitated yellow solid was filtered and dried. The product (420 mg, 40%) was used in the next step without further purification. 1H NMR (300 MHz, DMSO-D6) 8.84 (1H, d), 8.09 (1H, s), 7.97 (1H, d), 7.19 (1H, d), 6.85 (1H, d), 6.73 (1H, dd), 4.49 (2H, s), 2.69 (3H, s); MS (m/e)=262.0 [MH+].

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureUpon cooling
  4. filtrationthe precipitated yellow solid was filtered
  5. customdried
  6. customThe product (420 mg, 40%) was used in the next step without further purification

Sources & evidence

ORD record
ord-0ff34db3428f410099e12ce10553206f
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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