4-Aminobenzonitrile → HCID 8532015, compound

HRID 1524279Notes

Reaction equation

HRID 1524279 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 66653346HCID 66653346, compound

Product 1

HCID 8532015HCID 8532015, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Cool a solution of 3-((S)-1-carboxy-ethoxy)-benzoic acid methyl ester (0.32 g, 1.43 mmol) in pyridine (5 mL) to 0° C. and add 4-aminobenzonitrile (0.20 g 1.69 mmol) followed by phosphorous oxychloride (0.15 mL, 1.60 mmol). Stir the mixture at 0° C. for 1 hour then dilute with water and extract with EtOAc. Wash the combined organic portion with a 2N solution of hydrochloric acid then dry over anhydrous sodium sulfate and concentrate under reduced pressure to provide 0.42 g of 3-[(S)-1-(4-cyano-phenylcarbamoyl)-ethoxy]-benzoic acid methyl ester as a foam.

Workup

  1. extractionextract with EtOAc
  2. washWash the combined organic portion with a 2N solution of hydrochloric acid
  3. dry with materialthen dry over anhydrous sodium sulfate
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-60aea48ca19b4d909ad9bc7d817fae77
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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