Hydrochloric Acid → HCID 54511686, compound

HRID 1859681Notes

Reaction equation

HRID 1859681 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([N:13](C(=O)C)[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[CH:6]=1>O1CCCC1.CO>[CH3:2][O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([NH:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 543001583-[Acetyl-(3,5-dichlorophenyl)-amino]-4-methoxybenzoic acid methyl ester

Product 1

HCID 54511686HCID 54511686, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Concentrated HCl (45 mL) was added to a solution of 3-[acetyl-(3,5-dichlorophenyl)-amino]-4-methoxybenzoic acid methyl ester (11.46 g, 31.12 mmol) in a mixture of tetrahydro-furan (75 mL) and methanol (75 mL). The reaction was heated to reflux. After 3 days, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate and dried (MgSO4). The ethyl acetate was removed under reduced pressure to give the product (2.4 g); m.p. 134-135° C. after chromatography on silica gel in ethyl acetate followed by recrystallization from ether/hexane 1:9.

Workup

  1. temperatureThe reaction was heated to reflux
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customThe ethyl acetate was removed under reduced pressure

Sources & evidence

ORD record
ord-c2a26a2e7761432db950bb73109e23b9
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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