3-(Trifluoromethyl)benzoyl chloride → HCID 58552865, compound

HRID 520465Notes

Reaction equation

HRID 520465 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=O.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[O:5]=[C:4]1[O:6][C:20]([C:19]2[CH:23]=[CH:24][CH:25]=[C:17]([C:16]([F:15])([F:26])[F:27])[CH:18]=2)=[N:1][C:2]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]1=2

Participants

5

Reactant 3

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 516892Sodium BicarbonateHCID 27948122-amino-3-(methoxycarbonyl)benzoic acid

Product 1

HCID 58552865HCID 58552865, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-3-(methoxycarbonyl)benzoic acid 20 (1.16 g, 5.94 mmol) in pyridine (10 mL) was added 3-trifluoromethylbenzoyl chloride 2 (0.90 mL, 5.94 mmol). The reaction was stirred for 16 h, poured into sat. aq NaHCO3 (50 mL), extracted with dichloromethane (3×50 mL) and the combined organic layers were dried (MgSO4) and concentrated. Toluene (10 mL) was added and the solution was concentrated in vacuo. The crude residue was purified by MPLC eluting with pentane/EtOAc (10-50%) to give 42 (1.45 g, 70% yield).

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. dry with materialthe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated
  4. additionToluene (10 mL) was added
  5. concentrationthe solution was concentrated in vacuo
  6. customThe crude residue was purified by MPLC
  7. washeluting with pentane/EtOAc (10-50%)

Sources & evidence

ORD record
ord-66e26ac52e2742d7b7dc587188222fa9
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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