Ethyl 2-(4-hydroxy-3,5-dimethylphenyl)-8,9-dimethoxy-3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1-carboxylate → Ethyl 8-methoxy-9-hydroxy-2-(3,5-dimethyl-4-hydroxyphenyl)-3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1-carboxylate

HRID 585078Notes

Reaction equation

HRID 585078 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21]C)[CH:19]=4)[CH2:14][CH2:13][N:12]3[C:25]=2[CH3:26])=[CH:4][C:3]=1[CH3:32].Cl.N1C=CC=CC=1>C(OCC)(=O)C.Cl>[CH3:24][O:23][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][C:18]=1[OH:21])[C:11]1=[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:9]([C:5]3[CH:6]=[C:7]([CH3:8])[C:2]([OH:1])=[C:3]([CH3:32])[CH:4]=3)=[C:25]([CH3:26])[N:12]1[CH2:13][CH2:14]2

Participants

5

Reactant 2

HCID 9889193Ethyl 2-(4-hydroxy-3,5-dimethylphenyl)-8,9-dimethoxy-3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1-carboxylateHCID 10176127Pyridinium chloride

Product 1

HCID 10295721Ethyl 8-methoxy-9-hydroxy-2-(3,5-dimethyl-4-hydroxyphenyl)-3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1-carboxylate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

1 g (2.3 mmol) of ethyl 2-(4hydroxy-3,5-dimethylphenyl)-8,9-dimethoxy-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate (Example 1) was intimately mixed with 4 g of pyridine hydrochloride and heated to fusion at 150° C. The mixture was stirred at 150° C. for 20 min., then cooled to room temperature and dissolved in a mixture of ethyl acetate and dilute hydrochloric acid. The layers were separated, the aqueous layer was extracted with ethyl acetate, and the combined organic phases were washed with water, dried over Na2SO4, and the solvent was evaporated under reduced pressure. Column chromatography on silica gel using a dichloromethane/ethyl acetate 10:1 mixture as eluant afforded the title compounds ethyl 8-methoxy-9-hydroxy-2-(3,5-dimethyl-4-hydroxyphenyl)-3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1-carboxylate (Example 26):

Workup

  1. temperaturecooled to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e6218cb37d874be49c6a2fcb9aef1c82
Source dataset
uspto-grants-2005_08
Patent number
US06930114B2

Reaction notes

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