HCID 69551824, compound → HCID 69551823, compound

HRID 1833270Notes

Reaction equation

HRID 1833270 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][C:21]2[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([O:28][CH3:29])[CH:22]=2)=[N:8][CH2:7]1)=[O:5])[CH3:2]>[Pd].C1(C)C(C)=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][C:21]2[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([O:28][CH3:29])[CH:22]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 69551824HCID 69551824, compound

Product 1

HCID 69551823HCID 69551823, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A solution of 6,7-dimethoxy-1-(3-methoxy-5-methyl-benzyl)-3,4-dihydro-isoquinoline-4-carboxylic acid ethyl ester (0.73 g, 1.8 mmol) and 10% palladium on carbon (230 mg) in xylene (15 mL) was refluxed overnight. The reaction mixture was cooled, filtered through celite, and concentrated in vacuo to afford 6,7-dimethoxy-1-(3-methoxy-5-methyl-benzyl)-isoquinoline-4-carboxylic acid ethyl ester as a light brown oil (0.63 g, 89%). This material was used without further purification: 1H NMR (300 MHz) compatible.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba4bb19ea2a6485483b10dbcbc4efcee
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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