Acetate → HCID 22496413, compound

HRID 1816170Notes

Reaction equation

HRID 1816170 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=O.[Cl:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.CC([O-])=O.C([BH3-])#N.[Na+]>CO>[Cl:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][CH2:1][C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 175AcetateHCID 78124-ChloroanilineHCID 120884-Formylbenzoic acidHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22496413HCID 22496413, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

4-Formylbenzoic acid (15 g, 100 mmol) was suspended in methanol (500 mL) and 4-chloroaniline (12.7 g, 100 mmol) was added. The resulting suspension was heated at reflux temperature for 30 minutes and subsequently cooled to approximately 35° C. Acetic cid glacial (50 mL) was added followed by sodium cyanoborohydride (4.96 g, 80 mmol) in portions. The mixture was stirred at room temperature for 30 minutes. The mixture was concentrated in vacuo to approximately 150 mL by rotary evaporation. Water (150 mL) was added and the resulting suspension was stirred at room temperature for 16 hours. Filtration, washing with water and drying afforded 26.8 g (100%) 4-[(4-chlorophenylamino)-methyl]benzoic acid as a solid.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux temperature for 30 minutes
  3. concentrationThe mixture was concentrated in vacuo to approximately 150 mL by rotary evaporation
  4. additionWater (150 mL) was added
  5. stirringthe resulting suspension was stirred at room temperature for 16 hours
  6. filtrationFiltration
  7. washwashing with water
  8. customdrying

Sources & evidence

ORD record
ord-14423a7dcdd942f8b744b2874468853c
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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