4-Aminobenzonitrile → 3-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester

HRID 1524266Notes

Reaction equation

HRID 1524266 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21](O)=[O:22])[CH:14]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1.O>[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21](=[O:22])[NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 133964-AminobenzonitrileHCID 24813Phosphorus oxychlorideHCID 13816150[3-(Methoxycarbonyl)phenoxy]acetic acid

Product 1

HCID 81734983-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl esterYield 86.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Cool a solution of 4-aminobenzonitrile (0.48 g, 4.02 mmol) in pyridine (30 mL), to 0° C., and add 3-carboxymethoxy-benzoic acid methyl ester (0.79 g, 3.76 mmol) followed by phosphorous oxychloride (0.38 mL, 4.02 mmol). Stir the mixture at 0° C. for 2 h then dilute with water causing a solid to precipitate from solution. Collect the solid by filtration, wash with water, and dry on the filter pad to provide 1.01 g (81.0%) of 3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester.

Workup

  1. customto precipitate from solution
  2. customCollect the solid
  3. filtrationby filtration
  4. washwash with water
  5. customdry on the filter pad

Sources & evidence

ORD record
ord-2af8e12905354636b797bd4eb147e8b3
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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