Dichloromethane → HCID 66990214, compound

HRID 454500Notes

Reaction equation

HRID 454500 reaction equation
C(Cl)Cl.[C:4](OC(=O)C)(=[O:6])[CH3:5].[OH:11][C:12]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>N1C=CC=CC=1>[C:4]([O:11][C:12]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2×HCID 46316976HCID 46316976, compound

Product 1

HCID 66990214HCID 66990214, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Methylene chloride (5.0 mL), pyridine (0.25 mL), and acetic anhydride (0.19 mL) were sequentially added to the obtained 2-hydroxy-5-(pyridin-3-yl)benzoic acid, followed by heating to reflux for 1 hour. The reaction mixture was cooled to room temperature, and then pyridine (0.082 mL) and acetic anhydride (0.095 mL) were added thereto, followed by heating to reflux for 30 minutes. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 99-93% chloroform/methanol] to obtain 0.035 g of 2-acetoxy-5-(pyridin-3-yl)benzoic acid as a white solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1 hour
  3. temperatureby heating
  4. temperatureto reflux for 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 99-93% chloroform/methanol]

Sources & evidence

ORD record
ord-efe340ad6ef24b97a1b08173d1fc045f
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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