Hydrochloric Acid → HCID 54511686, compound

HRID 1387530Notes

Reaction equation

HRID 1387530 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 tetrahydrofuran (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-82a32adeb35345acbbd2ecd0eefd25fa
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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