4-Aminobenzonitrile → HCID 8532025, compound

HRID 1524275Notes

Reaction equation

HRID 1524275 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@@H:11]([C:13]([OH:15])=O)[CH3:12])[CH:5]=1.[NH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1.O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@@H:11]([C:13](=[O:15])[NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[CH3:12])[CH:5]=1

Participants

6

Reactant 3

HCID 133964-AminobenzonitrileHCID 24813Phosphorus oxychlorideHCID 66653136HCID 66653136, compound

Product 1

HCID 8532025HCID 8532025, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Cool a solution 3-((R)-1-carboxy-ethoxy)-benzoic acid methyl ester (0.50 g, 1.90 mmol) in pyridine (5 mL), to 0° C., and add 4-aminobenzonitrile (0.28 g, 2.33 mmol) followed by phosphorous oxychloride (0.22 mL, 2.4 mmol). Stir the mixture at 0° C. for 1 h then dilute with water and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography to provide 0.59 g of 3-[(R)-1-(4-cyano-phenylcarbamoyl)-ethoxyl]-benzoic acid methyl ester as an oil.

Workup

  1. concentrationconcentrate under reduced pressure
  2. customPurify the residue by flash silica gel chromatography

Sources & evidence

ORD record
ord-64f21f25009b4b3995ad9f1c719e5250
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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