Hydrochloric Acid → 3-[(3-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid

HRID 1524264Notes

Reaction equation

HRID 1524264 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14](=[O:24])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[CH:7]=1.CO.Cl>O>[C:22]([C:18]1[CH:17]=[C:16]([NH:15][C:14]([CH2:13][O:12][C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:5]([OH:25])=[O:4])=[O:24])[CH:21]=[CH:20][CH:19]=1)#[N:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 81732703-[(3-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester

Product 1

HCID 454172573-[(3-Cyano-phenylcarbamoyl)-methoxy]-benzoic acidYield 70.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add lithium hydroxide (0.15 g, 6.3 mmol) to a suspension of 3-[(3-cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester (0.94 g, 3.1 mmol) in a 1:1 mixture of MeOH:water (30 mL). Stir the mixture at room temperature for 15 h then adjust the pH of the reaction to slightly acidic by the addition of a 2 N solution of hydrochloric acid. A solid precipitates from solution. Collect by filtration, wash with water, and dry on the filter pad to provide 0.650 g of 3-[(3-cyano-phenylcarbamoyl)-methoxy]-benzoic acid as a solid.

Workup

  1. customthe pH of the reaction to
  2. customA solid precipitates from solution
  3. filtrationCollect by filtration
  4. washwash with water
  5. customdry on the filter pad

Sources & evidence

ORD record
ord-7dd970f8a8c249cbb477543f486bec6a
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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